Phenylacetonitrile (Benzyl cyanide; BnCN) [CAS 140-29-4; InChIKey SUSQOBVLVYHIEX-UHFFFAOYSA-N by Asch

Query Query

Results

Date

395 reactions in 2016-03-14 01h:49m:07s (EST) Reaxys

1. Query

Search as: As drawn

1/122

2016-03-14 02:10:57

C–

Na +

Rx-ID: 33406752 View in Reaxys 1/395 Yield

Conditions & References

87 %

3.6. Typical procedure for the nucleophilic substitution benzyl halides withNaCN General procedure: To amixture of the benzyl halide (1.0mmol) and NaCN (2mmol) inwater (5 mL), PEG-MDIL (0.2 g) was added. The suspension was magneticallystirred under reflux conditions for the time shown in Table 2.After completion of the reaction, the mixture was extracted with ether(2 × 10 mL). The combined organic extracts (dried over CaCl2) wereevaporated under reduced pressure. The desired benzyl cyanide wasobtained in good to excellent isolated yields (Scheme 3). With polyethylene glycol functionalized magnetic dicationic ionic liquid in water, Time= 0.916667h, Reflux, Green chemistry Godajdar, Bijan Mombani; Ansari, Bita; Journal of Molecular Liquids; vol. 202; (2015); p. 34 - 39 View in Reaxys

85 %

in ethanol, water, Time= 4h, Reflux Radulovic, Niko S.; Dekic, Milan S.; Stojanovic-Radic, Zorica Z.; Phytochemistry Letters; vol. 5; nb. 2; (2012); p. 351 - 357 View in Reaxys

82 %

Typical procedure for the nucleophilic substitution of benzylhalides catalyzed by β-CDPU-MNPs General procedure: To a mixture of the benzyl halide (1.0 mmol) and MY (Y:N3, SCN, OAc, CN) (2 mmol) in water (5 ml), -CDPU-MNPs (0.1 g) was added. The suspension was magnetically stirred under reflux conditions for the time shown in Table 1. After complete consumption of starting material as judged by TLC (using n-hexane–ethylacetate as eluent), the catalyst was concentrated on the sidewall of the reaction vessel using an external magnet, the aqueous phase was separated by decantation and extracted with diethyl ether (2× 10 mL). The extracted was dried with calcium chloride (CaCl2) and evaporated in vacuo to give corresponding product. The residual catalyst in the reaction vessel was washed and dried and then subjected to the next run directly With β-cyclodextrin-polyurethane polymercoated Fe3O4 magnetic nanoparticle in water, Time= 0.583333h, T= 90 °C Kiasat, Ali Reza; Nazari, Simin; Journal of Molecular Catalysis A: Chemical; vol. 365; (2012); p. 80 - 86 View in Reaxys 2.3 Typical procedure for the nucleophilic substitution reaction of benzyl halides with cyanide and azide anions in water catalyzed by β-CDPU General procedure: To a magnetically stirred mixture of the benzyl halide (1.0 mmol) and nucleophilic reagents (NaN3 or NaCN) (2 mmol) in water (5 mL), β-CDPU resin (0.2 g) was added. The resulting reaction mixture was stirred at 90 °C for the appropriate time. After completion of the reaction as indicated by TLC [using n-hexane/ethyl acetate (5:1)], the insoluble polymeric catalyst was filtered off and the filtrate was extracted with diethyl ether (2 × 10 mL). The organic phase was dried over calcium chloride, and evaporated in vacuo to give the product in 78–91percent isolated yields. All the compounds were characterized on the basis of spectroscopic data (IR, 1H & 13 C NMR) and by comparison with those reported in the literature [15,18]. With β-cyclodextrin-polyurethane resin in water, Time= 0.666667h, T= 90 °C Kiasat, Ali Reza; Nazari, Simin; Catalysis Communications; vol. 18; (2012); p. 102 - 105 View in Reaxys

92 %Chromat.

With Aliquatreg; 336 in water, Time= 1h, T= 40 °C Bielski, Roman; Joyce, Peter J.; Organic Process Research and Development; vol. 7; nb. 4; (2003); p. 551 - 552 View in Reaxys

C–

Na +

Rx-ID: 28748765 View in Reaxys 2/395

2/122

2016-03-14 02:10:57

Yield 88 %

Conditions & References 3.6. Typical procedure for the nucleophilic substitution benzyl halides withNaCN General procedure: To amixture of the benzyl halide (1.0mmol) and NaCN (2mmol) inwater (5 mL), PEG-MDIL (0.2 g) was added. The suspension was magneticallystirred under reflux conditions for the time shown in Table 2.After completion of the reaction, the mixture was extracted with ether(2 × 10 mL). The combined organic extracts (dried over CaCl2) wereevaporated under reduced pressure. The desired benzyl cyanide wasobtained in good to excellent isolated yields (Scheme 3). With polyethylene glycol functionalized magnetic dicationic ionic liquid in water, Time= 1h, Reflux, Green chemistry Godajdar, Bijan Mombani; Ansari, Bita; Journal of Molecular Liquids; vol. 202; (2015); p. 34 - 39 View in Reaxys

79 %

Typical procedure for the nucleophilic substitution of benzylhalides catalyzed by β-CDPU-MNPs General procedure: To a mixture of the benzyl halide (1.0 mmol) and MY (Y:N3, SCN, OAc, CN) (2 mmol) in water (5 ml), -CDPU-MNPs (0.1 g) was added. The suspension was magnetically stirred under reflux conditions for the time shown in Table 1. After complete consumption of starting material as judged by TLC (using n-hexane–ethylacetate as eluent), the catalyst was concentrated on the sidewall of the reaction vessel using an external magnet, the aqueous phase was separated by decantation and extracted with diethyl ether (2× 10 mL). The extracted was dried with calcium chloride (CaCl2) and evaporated in vacuo to give corresponding product. The residual catalyst in the reaction vessel was washed and dried and then subjected to the next run directly. With β-cyclodextrin-polyurethane polymercoated Fe3O4 magnetic nanoparticle in water, Time= 0.416667h, T= 90 °C Kiasat, Ali Reza; Nazari, Simin; Journal of Molecular Catalysis A: Chemical; vol. 365; (2012); p. 80 - 86 View in Reaxys 1 :A mixture of compound 1 (17.1 g, 0.1 mol) and NaCN (5.39 g, 0.11 mol) in 50 mL of ethanol and 300 mL of water was heated (oil bath 98-100° C.) for 5 h. The mixture was cooled, concentrated to remove ethanol, and extracted with ethyl acetate. The organic phase was washed with brine, dried (Na2SO4) and concentrated. Distillation gave 9.25 g of compound 2. in ethanol, water, Time= 5h, Heating Patent; INTERMUNE, INC.; US2009/257979; (2009); (A1) English View in Reaxys 2.3 Typical procedure for the nucleophilic substitution reaction of benzyl halides with cyanide and azide anions in water catalyzed by β-CDPU General procedure: To a magnetically stirred mixture of the benzyl halide (1.0 mmol) and nucleophilic reagents (NaN3 or NaCN) (2 mmol) in water (5 mL), β-CDPU resin (0.2 g) was added. The resulting reaction mixture was stirred at 90 °C for the appropriate time. After completion of the reaction as indicated by TLC [using n-hexane/ethyl acetate (5:1)], the insoluble polymeric catalyst was filtered off and the filtrate was extracted with diethyl ether (2 × 10 mL). The organic phase was dried over calcium chloride, and evaporated in vacuo to give the product in 78–91percent isolated yields. All the compounds were characterized on the basis of spectroscopic data (IR, 1H & 13 C NMR) and by comparison with those reported in the literature [15,18]. With β-cyclodextrin-polyurethane resin in water, Time= 0.583333h, T= 90 °C Kiasat, Ali Reza; Nazari, Simin; Catalysis Communications; vol. 18; (2012); p. 102 - 105 View in Reaxys

Rx-ID: 31423979 View in Reaxys 3/395 Yield 90 %

Conditions & References General procedure for oxidative fragmentation of oxiranes. General procedure: To a stirred solution of IBX (10.0 mmol) in aqueous ammonia (25 mL of a 28-30percent solution) was added oxirane (5.0 mmol) in 5 mL of acetonitrile in one portion. The reaction mixture was stirred at 70 °C until complete consumption of starting material as observed on TLC (up to 4 h). After completion of reaction, the reaction mixture was extracted with chloroform (2 .x. 15 mL). The organic layer was washed with water (2 .x. 10 mL); bisulfate

3/122

2016-03-14 02:10:57

solution (15 mL) followed by water (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude product. Pure product was obtained after column chromatography (silica gel, mesh size 60-120, eluent ethyl acetate/hexane 05:95). With ammonia, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in water, acetonitrile, T= 70 °C Deshmukh, Swapnil S.; Huddar, Sameerana N.; Jadhav, Ravindra R.; Akamanchi, Krishnacharya G.; Tetrahedron Letters; vol. 52; nb. 35; (2011); p. 4533 - 4536 View in Reaxys 85 %

With ammonia, iodine in water, acetonitrile, T= 70 °C Jadhav, Ravindra R.; Akamanchi, Krishnacharya G.; Chemistry Letters; vol. 42; nb. 2; (2013); p. 162 - 164 View in Reaxys

N O

Rx-ID: 66203 View in Reaxys 4/395 Yield

Conditions & References

92 %

With anhydrous ammonium carbonate, diphosphorous tetraiodide in carbon disulfide, Time= 6h, T= 20 °C Telvekar, Vikas N.; Rane, Rajesh A.; Tetrahedron Letters; vol. 48; nb. 34; (2007); p. 6051 - 6053 View in Reaxys

92 %

With hydroxylammonium sulphate, zinc, Time= 0.333333h, Microwave irradiation Cao, Yu-Qing; Qu, An-Li; Liu, Rui-Yan; Duan, Chun-Ming; Journal of Chemical Research; nb. 7; (2010); p. 414 415 View in Reaxys

88 %

With sodium azide, TEA, diethylphosphinoethane, [bis(2-methoxyethyl)amino]-sulfur trifluoride in dichloromethane, dimethyl sulfoxide, Time= 30h, T= 0 °C Kangani, Cyrous O.; Day, Billy W.; Kelley, David E.; Tetrahedron Letters; vol. 49; nb. 5; (2008); p. 914 - 918 View in Reaxys

72 %

With aluminum oxide, aminosulfonic acid, urea, Time= 0.216667h, Irradiation Juncai, Feng; Bin, Liu; Yang, Lhi; Changchuan, Li; Synthetic Communications; vol. 26; nb. 24; (1996); p. 4545 4548 View in Reaxys With ammonia, T= 500 °C , Leiten ueber Silicagel Mitchell; Reid; Journal of the American Chemical Society; vol. 53; (1931); p. 327 View in Reaxys

C–

N N+

Rx-ID: 29502572 View in Reaxys 5/395 Yield 95 %

Conditions & References With H3[PW12O40], Time= 0.0333333h, T= 130 - 142 °C , Microwave irradiation, Ionic liquid, chemoselective reaction Mohammadpoor-Baltork, Iraj; Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiolah; Mirjafari, Arsalan; Comptes Rendus Chimie; vol. 13; nb. 12; (2010); p. 1468 - 1473 View in Reaxys

89 %

General procedure: A mixture of MOM–ethers (1 mmol) [Bu4N][X](2 mmol) was added to [Hmim][NO3] (0.4 mmol) (and exposed to MWirradiation (All reactions were carried out at 135-140 oC with 170 Wapplied power). After completion of

4/122

2016-03-14 02:10:57

the reactions (monitored by TLC, eluent:n–hexane/ethyl acetate, 5:1), the mixture was extracted with Et2O(3×10 mL). The organic phase was dried over anhydrous Na2SO4and rotary evaporation afforded a residue, which was then passed through ashort pad of neutral alumina (n–hexane/ethyl acetate, 5:1, 75 mL) to obtain thehighly pure products. The spectral data were inaccordance with those reported in the literature: With [Hmim][NO3], Time= 0.05h, T= 135 - 140 °C , Microwave irradiation, Reagent/catalyst Noei, Jalil; Mirjafari, Arsalan; Tetrahedron Letters; vol. 55; nb. 32; (2014); p. 4424 - 4426 View in Reaxys 88 %

With [bmim][InCl4], Time= 0.075h, T= 135 - 140 °C , Microwave irradiation, Neat (no solvent), chemoselective reaction Mirjafari, Arsalan; Mohammadpoor-Baltork, Iraj; Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Khosropour, Ahmad Reza; Tetrahedron Letters; vol. 51; nb. 25; (2010); p. 3274 - 3276 View in Reaxys

88 %

With C6H5C(Me)2OMOM, [bmim][InCl4], Time= 0.075h, T= 135 - 140 °C , Microwave irradiation, Neat (no solvent), chemoselective reaction Mirjafari, Arsalan; Mohammadpoor-Baltork, Iraj; Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Khosropour, Ahmad Reza; Tetrahedron Letters; vol. 51; nb. 25; (2010); p. 3274 - 3276 View in Reaxys

88 %

With (methoxymethyleneoxy)phenol, [bmim][InCl4], Time= 0.075h, T= 135 - 140 °C , Microwave irradiation, Neat (no solvent), chemoselective reaction Mirjafari, Arsalan; Mohammadpoor-Baltork, Iraj; Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Khosropour, Ahmad Reza; Tetrahedron Letters; vol. 51; nb. 25; (2010); p. 3274 - 3276 View in Reaxys

N N

Rx-ID: 38207252 View in Reaxys 6/395 Yield 87 %

Conditions & References Synthesis of nitriles from 2-substituted-1,3,4-oxadiazoles; general procedure General procedure: A mixture of 2-substituted-1,3,4-oxadiazole (0.5 mmol), t-BuONa (0.5 mmol) and DMF or DMSO (1 mL) was stirred at room temperaturefor an appropriate time. When the reaction completed, EtOAc (5 mL) and petroleum ether (5 mL) were added, and the mixture was washed by water (3 × 10 mL) to remove DMF or DMSO. The organic layer was collected and filtered through a bed of silica gel layered over Celite.The volatiles were removed under reduced pressure to afford the final product. In a few cases, further column chromatography on silica gel was needed to afford the pure desired product. With sodium t-butanolate in N,N-dimethyl-formamide, Time= 4h, T= 20 °C Lu, Guo-Ping; Lin, Ya-Mei; Journal of Chemical Research; vol. 38; nb. 6; (2014); p. 371 - 374 View in Reaxys

Rx-ID: 713227 View in Reaxys 7/395 Yield

Conditions & References

70 %, 10 % With sodium hexamethyldisilazane, Verkade nonionic superbase, palladium diacetate in toluene, Time= 15h, T= 90 °C You, Jingsong; Verkade, John G.; Angewandte Chemie - International Edition; vol. 42; nb. 41; (2003); p. 5051 - 5053

5/122

2016-03-14 02:10:57

View in Reaxys With ammonia, KNH2 Bergstrom; Agostinho; Journal of the American Chemical Society; vol. 67; (1945); p. 2153 View in Reaxys 2H 2H

Rx-ID: 2409707 View in Reaxys 8/395 Yield 91 %

Conditions & References With water-d2, potassium carbonate, Time= 24h, T= 50 °C Wimalasena, Kandatege; Alliston, Kevin R.; Journal of the American Chemical Society; vol. 117; nb. 4; (1995); p. 1220 - 1224 View in Reaxys With water-d2 Wimalasena, Kandatege; May, Sheldon W.; Journal of the American Chemical Society; vol. 111; nb. 7; (1989); p. 2729 - 2731 View in Reaxys With sodium cyanide, water-d2 in 1,4-dioxane, Time= 6h, Ambient temperature Wierlacher, Stefan; Sander, Wolfram; Uu, Michael T. H.; Journal of the American Chemical Society; vol. 115; nb. 20; (1993); p. 8943 - 8953 View in Reaxys With NaOD, tetrabutylammomium bromide in water, Time= 2h, Ambient temperature Kim, Sung Soo; Tuchkin, Alexey; Journal of Organic Chemistry; vol. 64; nb. 11; (1999); p. 3821 - 3824 View in Reaxys

5.4 g

With potassium tert-butylate, water-d2, T= 20 °C Ito, Yoshikatsu; Nakabayashi, Hironari; Ohba, Shigeru; Hosomi, Hiroyuki; Tetrahedron; vol. 56; nb. 37; (2000); p. 7139 - 7152 View in Reaxys

Rx-ID: 5000080 View in Reaxys 9/395 Yield 100 %

Conditions & References With N-Methyl-2-pyrrolidone, hydroxylamine hydrochloride, Time= 0.25h, T= 100 °C , microwave irradiation, Condensation Chakraborti, Asit K.; Kaur, Gurmeet; Tetrahedron; vol. 55; nb. 46; (1999); p. 13265 - 13268 View in Reaxys

100 %

With hydroxylamine hydrochloride in N-Methyl-2-pyrrolidone, Time= 0.0833333h, T= 100 °C Chakraborti; Kaur; Roy; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 40; nb. 10; (2001); p. 1000 - 1006 View in Reaxys

95 %

13 A typical method for preparation of nitrile from aldehyde using AHA: General procedure: 4-Isopropylbenzaldehyde 1a (0.50 g, 3.37 mmol), acetohydroxamic acid (0.30 g, 4.05 mmol), acetonitrile (5 ml), and Bi(OTf)3 (0.11 g, 0.17 mmol) were taken into a 25 ml round-bottomed flask fitted with a condenser and calcium chloride guard tube. The mixture was refluxed for 14 h and after completion of the reaction (GC, 10percent SE-30 on Chromosorb, 10' .x. 1/8 column), the reaction mixture was cooled to room temperature and the solvent was

6/122

2016-03-14 02:10:57

removed under reduced pressure. The crude product obtained was purified by normal column chromatography(silica gel 100-200 mesh, ethyl acetate/hexane = 1:20) to obtain 4-isopropylbenzonitrile 3a (0.47 g, 97percent). With bismuth trifluoromethanesulphonate, acetylhydroxamic acid in acetonitrile, Time= 16h, Reflux Sridhar, Madabhushi; Reddy, Mallu Kishore Kumar; Sairam, Vangipuram Venkata; Raveendra, Jillella; Godala, Kondal Reddy; Narsaiah, Chinthala; Ramanaiah, Beeram China; Reddy, Cirandur Suresh; Tetrahedron Letters; vol. 53; nb. 27; (2012); p. 3421 - 3424 View in Reaxys 92 %

With ammonium hydroxide, Time= 6h, T= 25 °C Telvekar, Vikas N.; Patel, Kavit N.; Kundaikar, Harish S.; Chaudhari, Hemchandra K.; Tetrahedron Letters; vol. 49; nb. 14; (2008); p. 2213 - 2215 View in Reaxys

92 %

General procedure for the synthesis of nitriles: A pressure tube was charged with an appropriate amount of Zn(OTf)2 (0.036 mmol, 5.0 mol percent), the corresponding aldehyde (0.72 mmol) and hydroxylamine hydrochloride (1.2 equiv, 0.86 mmol). After the addition of toluene (2.0 mL) the reaction mixture was stirred in a preheated oil bath at 100 °C for 24 h. The mixture was cooled in an ice bath and biphenyl (internal standard) was added. The solution was diluted with dichloromethane and an aliquot was taken for GC-analysis (30 m Rxi-5 ms column, 40-300 °C). The solvent was carefully removed and the residue was purified by column chromatography (n-hexane/ethyl acetate). The analytical properties of the corresponding nitriles are in agreement with the literature. With hydroxylamine hydrochloride, zinc trifluoromethanesulfonate in toluene, Time= 24h, T= 100 °C Enthaler, Stephan; Weidauer, Maik; Schroeder, Fanny; Tetrahedron Letters; vol. 53; nb. 7; (2012); p. 882 - 885 View in Reaxys

91 %

With [hydroxy(tosyloxy)iodo]benzene, ammonium acetate in water, acetonitrile, Time= 3h, T= 80 °C Zhu, Chenjie; Sun, Chengguo; Wei, Yunyang; Synthesis; nb. 24; (2010); p. 4235 - 4241; Art.No: F14610SS View in Reaxys

90 %

With ammonium hydroxide, bis(trifluoroacetato)-phenyliodine in water, Time= 0.583333h, T= 25 °C Telvekar, Vikas N.; Rane, Rajesh A.; Namjoshi, Tejal V.; Synthetic Communications; vol. 40; nb. 4; (2010); p. 494 - 497 View in Reaxys

87 %

With aluminum oxide, hydroxylamine hydrochloride, di(n-butyl)tin oxide, Time= 0.0666667h, microwave irradiation Yadav; Subba Reddy; Madan; Journal of Chemical Research - Part S; nb. 5; (2001); p. 190 - 191 View in Reaxys

83 %

With aluminum oxide, Oxonereg;, hydroxylamine hydrochloride in solid, Time= 0.166667h, microwave irradiation Bose, D. Subhas; Narsaiah, A. Venkat; Tetrahedron Letters; vol. 39; nb. 36; (1998); p. 6533 - 6534 View in Reaxys

82 %

With aluminum oxide, potassium fluoride, hydroxylamine hydrochloride in DMFA, Time= 10.5h, T= 100 °C Movassagh, Barahman; Shokri, Salman; Tetrahedron Letters; vol. 46; nb. 40; (2005); p. 6923 - 6925 View in Reaxys

82 %

With tert -butyl hydrogen peroxide, ammonium hydroxide, tetra-(n-butyl)ammonium iodide in water, Time= 16h, T= 80 °C , Catalytic behavior Wang, Liang; Shen, Chen; Wang, Hai-Ping; Zhou, Wei-You; Sun, Fu-An; He, Ming-Yang; Chen, Qun; Journal of Chemical Research; vol. 36; nb. 8; (2012); p. 460 - 462 View in Reaxys

81 %

With (diacetoxyiodo)benzene, ammonium acetate, sodium lauryl sulfate in water, Time= 5h, T= 70 °C Zhu, Chenjie; Ji, Lei; Wei, Yunyang; Synthesis; nb. 18; (2010); p. 3121 - 3125 View in Reaxys

7/122

2016-03-14 02:10:57

77 %

Benzonitrile by One-Pot Synthesis from Benzaldehyde; Typical Procedures General procedure: Microwave irradiation: A mixture of benzaldehyde (0.106 g, 1 mmol), hydroxylamine hydrochloride (0.083 g, 1.2 mmol) and catalyst (15 molpercent) was irradiated in microwave oven at 140 °C for 10 min. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mass was cooled to r.t. The product was extracted into EtOAc. The solid product was obtained after evaporation of EtOAc. The obtained solid was purified by column chromatography (silica gel). The pure product was characterized by GC-MS and 1H NMR. With (2-hydroxyethyl)trimethylazanium urea chloride, hydroxylamine hydrochloride in neat (no solvent), Time= 0.166667h, T= 140 °C , Microwave irradiation, Green chemistry Patil, Umakant B.; Shendage, Suresh S.; Nagarkar, Jayashree M.; Synthesis (Germany); vol. 45; nb. 23; (2013); p. 3295 - 3299 View in Reaxys With ammonia, iodine in tetrahydrofuran, water, Time= 1h, T= 20 °C Reddy, M.B.Madhusudana; Pasha; Synthetic Communications; vol. 41; nb. 14; (2011); p. 2081 - 2085 View in Reaxys Reaction Steps: 3 1: ammonia / water / 20 °C / |Green chemistry 2: iodine / water / 20 °C / |Green chemistry 3: ammonia / water / 20 °C / |Green chemistry With ammonia, iodine in water Yadav, Arvind K.; Srivastava, Vishnu P.; Yadav, Lal Dhar S.; Synthetic Communications; vol. 44; nb. 3; (2014); p. 408 - 416 View in Reaxys Reaction Steps: 2 1: triethylamine; hydroxylamine hydrochloride / dichloromethane / 16 h / 20 °C / |Inert atmosphere 2: Xtalfluor-E®; triethylamine / ethyl acetate / 1 h / 20 °C / |Inert atmosphere With hydroxylamine hydrochloride, triethylamine, Xtalfluor-E® in dichloromethane, ethyl acetate Keita, Massaba; Vandamme, Mathilde; Paquin, Jean-Franois; Synthesis (Germany); vol. 47; nb. 23; (2015); p. 3758 - 3766; Art.No: SS-2015-M0394-OP View in Reaxys

N HO N

Rx-ID: 2059741 View in Reaxys 10/395 Yield 95 %

Conditions & References With trifluoromethanesulfonic acid anhydride, triethylamine, triphenylphosphine in dichloromethane, Time= 0.166667h, T= 0 °C Moussa, Ziad; Ahmed, Saleh A.; ElDouhaibi, Ahmad S.; Al-Raqa, Shaya Y.; Tetrahedron Letters; vol. 51; nb. 14; (2010); p. 1826 - 1831 View in Reaxys

89 %

With iodine, triphenylphosphine in dichloromethane, Time= 5h, T= 20 °C Venkat Narsaiah; Sreenu; Nagaiah; Synthetic Communications; vol. 36; nb. 2; (2006); p. 137 - 140 View in Reaxys

87 %

With oxalyl dichloride, Bis-lt;(p-methoxy)phenylgt;cyclopropenon, DBU in dichloromethane, Time= 5.5h, Reflux Rai, Ankita; Yadav, Lal Dhar S.; European Journal of Organic Chemistry; nb. 10; (2013); p. 1889 - 1893 View in Reaxys

86 %

With aluminium(III) iodide in acetonitrile, Time= 3h, Heating Konwar, Dilip; Boruah, Romesh C.; Sandhu, Jagir S.; Tetrahedron Letters; vol. 31; nb. 7; (1990); p. 1063 - 1064

8/122

2016-03-14 02:10:57

View in Reaxys 86 %

With phosgene dimer in acetonitrile, Time= 0.0833333h Mai, Khuong; Path, Ghanshyam; Synthesis; nb. 12; (1986); p. 1037 - 1038 View in Reaxys

86 %

With 2,4,5,7-tetrabromofluorescein, carbon tetrabromide, DMFA in acetonitrile, Time= 16h, T= 25 °C , Irradiation, Inert atmosphere Yadav, Arvind K.; Srivastava, Vishnu P.; Yadav, Lal Dhar S.; RSC Advances; vol. 4; nb. 8; (2014); p. 4181 - 4186 View in Reaxys

85 %

With DBU, p-toluenesulfonyl imidazole in DMFA, Time= 0.666667h, Reflux Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthetic Communications; vol. 40; nb. 16; (2010); p. 2429 - 2440 View in Reaxys

84 %

With trimethylsilyl iodide, bis(trimethylsilyl)amine in chloroform, Time= 4h, T= 56 °C Jung, Michael E.; Long-Mei, Zeng; Tetrahedron Letters; vol. 24; nb. 42; (1983); p. 4533 - 4534 View in Reaxys

84 %

With 4,6-diphenyl-2-methylthio-pyrylium tetrafluoroborate, triethylamine in dichloromethane, Time= 24h Molina, P.; Alajarin, M.; Vilaplana, M. J.; Synthesis; nb. 12; (1982); p. 1016 - 1017 View in Reaxys

84 %

With trimethylsilyl iodide, bis(trimethylsilyl)amine in chloroform, Time= 4h, T= 56 °C , other temperature, without hexamethyldisilazane (TMS2NH), Product distribution Jung, Michael E.; Long-Mei, Zeng; Tetrahedron Letters; vol. 24; nb. 42; (1983); p. 4533 - 4534 View in Reaxys

83 %

With phosphorus(III) iodide, triethylamine in dichloromethane, Time= 0.25h, T= 25 °C Denis, Jean Noel; Krief, Alain; Journal of the Chemical Society, Chemical Communications; nb. 12; (1980); p. 544 545 View in Reaxys

81 %

With 1,4-diaza-bicyclo[2.2.2]octane, imidazole, phosgene, titanium acetate, formyl acetic anhydride, 1) DMF, 25 deg C, 18 h, 2) methylene dichloride, 0 deg C Barton, H. R. Derek; Bowles, Timothy; Husinec, Suren; Forbes, Judith E.; Llobera, Antonia; et al.; Tetrahedron Letters; vol. 29; nb. 27; (1988); p. 3343 - 3346 View in Reaxys

81 %

With dimethyl dithiocarbonate, triethylamine in 1,4-dioxane, T= 90 °C Khan, Taukeer Ahmad; Peruncheralathan, Saravanan; Ila, Hiriyakkanavar; Junjappa, Hiriyakkanavar; Synlett; nb. 11; (2004); p. 2019 - 2021 View in Reaxys

80 %

With potassium fluoride on basic alumina in DMFA, Time= 12h, T= 85 °C Movassagh, Barahman; Shokri, Salman; Synthetic Communications; vol. 35; nb. 6; (2005); p. 887 - 890 View in Reaxys

74 %

Representative procedure for nitrile synthesis General procedure: In an oven-dried two-necked 50 mLround-bottomed flask, equipped with a stirring bar, a solution of the oxime(1.0 mmol) and 2-NO2-C6H4-SO3XY(1.5 mmol) dissolved in anhydrous CH2Cl2 (5.0 mL) wasplaced under the atmosphere of nitrogen. The reaction mixture was stirred atroom temperature for 5 min, then DBU (2.5 mmol) was added drop wise over 2 min.The reaction mixture became a clear homogeneous solution after addition of DBU.The reaction was monitored by TLC. The reaction mixture was diluted with EtOAcand washed with water (2×5 mL) followed by brine (2×5 mL) upon completeconsumption of the starting material. Product was purified by columnchromatography.Furthermore, the by-product Oxymacould be readily recovered by acidifying the aqueous layer, and then extrac-

9/122

2016-03-14 02:10:57

tingwith ethyl acetate. The Oxyma thus recovered can then be reused to regeneratethe sulfonate ester of Oxyma, which can be further used for a separate batch ofreaction. With (E)-ethyl 2-cyano-2-(2-nitrophenylsulfonyloxyimino)acetate, DBU in dichloromethane, T= 20 °C , Inert atmosphere Dev, Dharm; Palakurthy, Nani Babu; Kumar, Nitesh; Mandal, Bhubaneswar; Tetrahedron Letters; vol. 54; nb. 33; (2013); p. 4397 - 4400 View in Reaxys 56 %

With palladium diacetate, caesium carbonate, triphenylphosphine in acetonitrile, Time= 3h, Reflux Kim, Hoo Sook; Kim, Sung Hwan; Kim, Jae Nyoung; Tetrahedron Letters; vol. 50; nb. 15; (2009); p. 1717 - 1719 View in Reaxys

52 %

Dehydration of Oximes and Amides to Nitriles; General Procedure General procedure: To a solution of the aldoxime or the amide (1.0 mmol) and Et3N (1.5mmol) in EtOAc (1 mL, 1 M) at r.t. was added XtalFluor-E8 (1.1 mmol)portionwise over ca. 2 min. The resulting solution was stirred at r.t.for 1 h. The reaction mixture was quenched with sat. aq Na2CO3 and extracted with CH2Cl2 (2 × 10 mL). The combined organic layers were washed with H2O and brine, dried (MgSO4), and concentrated under vacuum to afford the crude nitrile, which was purified by flash chromatography, if required. With triethylamine, Xtalfluor-E® in ethyl acetate, Time= 1h, T= 20 °C , Inert atmosphere Keita, Massaba; Vandamme, Mathilde; Paquin, Jean-Franois; Synthesis (Germany); vol. 47; nb. 23; (2015); p. 3758 - 3766; Art.No: SS-2015-M0394-OP View in Reaxys With potassium hydroxide, chloroform, water, N-hexadecyl-N,N,N-trimethylammonium bromide, Time= 1h, Heating, Yield given Jursic, Branko; Synthetic Communications; vol. 19; nb. 3and4; (1989); p. 689 - 694 View in Reaxys With pyridine, triethylamine, dicyclohexyl-carbodiimide in tetrahydrofuran, diethyl ether, hexane, dichloromethane, Time= 12h, T= 20 °C , Inert atmosphere Sengupta, Ritobroto; Weinreb, Steven M.; Synthesis (Germany); vol. 44; nb. 18; (2012); p. 2933 - 2937 View in Reaxys

N H 2N

Rx-ID: 663139 View in Reaxys 11/395 Yield 97 %

Conditions & References With nickel sulphate, sodium hydroxide, dipotassium peroxodisulfate in dichloromethane, Time= 24h, Ambient temperature Yamazaki; Bulletin of the Chemical Society of Japan; vol. 63; nb. 1; (1990); p. 301 - 303 View in Reaxys

95 %

With TEA, trichloroisocyanuric acid in N,N-dimethyl-formamide, Time= 4h, T= 15 °C De Luca, Lidia; Giacomelli, Giampaolo; Synlett; nb. 12; (2004); p. 2180 - 2184 View in Reaxys

95 %

With TCBDA, triethylamine in N,N-dimethyl-formamide, Time= 2h, T= 25 °C Ghorbani-Vaghei, Ramin; Veisi, Hojat; Synthesis; nb. 6; (2009); p. 945 - 950; Art.No: Z23008ST View in Reaxys

92 %

With tetrabutylammomium bromide, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in acetonitrile, Time= 0.0833333h, T= 20 °C , Inert atmosphere, Molecular sieve

10/122

2016-03-14 02:10:57

Drouet, Fleur; Fontaine, Patrice; Masson, Geraldine; Zhu, Jieping; Synthesis; nb. 8; (2009); p. 1370 - 1374; Art.No: T19708SS View in Reaxys 85 %

With trichloroisocyanuric acid, ammonia in water, T= 20 - 60 °C Veisi, Hojat; Synthesis; nb. 15; (2010); p. 2631 - 2635; Art.No: Z04110SS View in Reaxys

75 %

With (hydroxy(tosyloxy)iodo)benzene, ammonium acetate in water, acetonitrile, Time= 4h, T= 80 °C Zhu, Chenjie; Sun, Chengguo; Wei, Yunyang; Synthesis; nb. 24; (2010); p. 4235 - 4241; Art.No: F14610SS View in Reaxys

65 %

With HRu(1,3-bis(6'-methyl-2'-pyridylimino)isoindoline)(PPh3)2 in toluene, Time= 24h, T= 110 °C , Inert atmosphere, Glovebox, chemoselective reaction Tseng, Kuei-Nin T.; Rizzi, Andrew M.; Szymczak, Nathaniel K.; Journal of the American Chemical Society; vol. 135; nb. 44; (2013); p. 16352 - 16355 View in Reaxys

56 %

With iodine, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide, Time= 1.5h, T= 65 °C Chiampanichayakul, Supanimit; Pohmakotr, Manat; Reutrakul, Vichai; Jaipetch, Thaworn; Kuhakarn, Chutima; Synthesis; nb. 13; (2008); p. 2045 - 2048 View in Reaxys With ammonia, T= 225 °C , Leiten ueber einen Nickel-Katalysator Mignonac; Annales de Chimie (Cachan, France); vol. <11> 2; (1934); p. 225,242 View in Reaxys

55 % Chro- With 2,6-dimethylpyridine, 2,2,6,6-tetramethyl-piperidine-N-oxyl, lithium perchlorate in acetonitrile, T= 23 °C , elecmat. trolysis, a platinum gauze electrode, +0.33 V (vs. Ag/Ag(1+)) Semmelhack, M. F.; Schmid, Christopher R.; Journal of the American Chemical Society; vol. 105; nb. 22; (1983); p. 6732 - 6734 View in Reaxys 74.5 % Turnov.

With TEMPO-modified graphite felt electrode in acetonitrile Kashiwagi, Yoshitomo; Kurashima, Futoshi; Kikuchi, Chikara; Anzai, Jun-Ichi; Osa, Tetsuo; Bobbitt, James M.; Journal of the Chinese Chemical Society; vol. 45; nb. 1; (1998); p. 135 - 138 View in Reaxys

97 % Chro- With sodium hydroxide, dipotassium peroxodisulfate, N-lauryl-N,N-dimethylamine oxide, nickel sulphate in water, mat. Time= 2h, T= 20 °C , pH= 12.9 Biondini, Daniele; Brinchi, Lucia; Germani, Raimondo; Goracci, Laura; Savelli, Gianfranco; European Journal of Organic Chemistry; nb. 14; (2005); p. 3060 - 3063 View in Reaxys

O N NH 2

Rx-ID: 664667 View in Reaxys 12/395 Yield 98 %

Conditions & References With allyl bromide, 1,1'-carbonyldiimidazole in acetonitrile, 1.) 0.5 h, RT; 2.) 2 h, reflux Kamijo, Tetsuhide; Harada, Hiromu; Iizuka, Kinji; Chemical & Pharmaceutical Bulletin; vol. 32; nb. 7; (1984); p. 2560 - 2564 View in Reaxys

98 %

With allyl bromide, 1,1'-carbonyldiimidazole in acetonitrile, further carboxamides, further reactive halides, Product distribution, Mechanism

11/122

2016-03-14 02:10:57

Kamijo, Tetsuhide; Harada, Hiromu; Iizuka, Kinji; Chemical & Pharmaceutical Bulletin; vol. 32; nb. 7; (1984); p. 2560 - 2564 View in Reaxys 94 %

With diethoxymethylane, [Et3NH][HFe3(CO)11] in 1,4-dioxane, Time= 4h, T= 100 °C , Inert atmosphere Zhou, Shaolin; Addis, Daniele; Das, Shoubhik; Junge, Kathrin; Beller, Matthias; Chemical Communications; nb. 32; (2009); p. 4883 - 4885 View in Reaxys

93 %

With FeCl2*4H2O, N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide in tetrahydrofuran, Time= 2h, T= 70 °C Enthaler, Stephan; European Journal of Organic Chemistry; nb. 25; (2011); p. 4760 - 4763 View in Reaxys

92 %

With N-chloro-succinimide, triphenylphosphine in tetrahydrofuran, Time= 4h, Heating Sugimoto, Osamu; Mori, Miho; Moriya, Keisuke; Tanji, Ken-Ichi; Helvetica Chimica Acta; vol. 84; nb. 5; (2001); p. 1112 - 1118 View in Reaxys

91 %

With MeSO3SiMe3, phosphorus pentoxide, Time= 3h, T= 70 - 75 °C , further reagents Rao, C. Someswara; Rambabu, M.; Srinivasan, P. S.; Synthetic Communications; vol. 19; nb. 7,8; (1989); p. 1431 - 1436 View in Reaxys

91 %

With UO2(NO3)2·6H2O, N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide in DME, Time= 24h, T= 100 °C Enthaler, Stephan; Chemistry - A European Journal; vol. 17; nb. 34; (2011); p. 9316 - 9319 View in Reaxys

90 %

With diethyl chlorophosphate, Time= 0.166667h, T= 120 °C , Neat (no solvent) Shahsavari-Fard; Sardarian; Journal of the Iranian Chemical Society; vol. 8; nb. 1; (2011); p. 204 - 208 View in Reaxys

89 %

With triethylamine, trifluoroacetyl chloride in dichloromethane Saednya, Akbar; Synthesis; nb. 2; (1985); p. 184 - 185 View in Reaxys

87 %

With phenylsilane, tetrabutyl ammonium fluoride in tetrahydrofuran, toluene, Time= 0.5h, T= 100 °C , Inert atmosphere Zhou, Shaolin; Junge, Kathrin; Addis, Daniele; Das, Shoubhik; Beller, Matthias; Organic Letters; vol. 11; nb. 11; (2009); p. 2461 - 2464 View in Reaxys

87 %

With N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide, zinc trifluoromethanesulfonate in tetrahydrofuran, Time= 24h, T= 70 °C , chemoselective reaction Enthaler, Stephan; Inoue, Shigeyoshi; Chemistry - An Asian Journal; vol. 7; nb. 1; (2012); p. 169 - 175 View in Reaxys

86 %

With pyridine, phenyl chloroformate in dichloromethane, T= 0 - 20 °C Bose; Varadarajan; Vanajatha; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 40; nb. 8; (2001); p. 722 - 723 View in Reaxys

84 %

With pyridine, aryl chlorothionoformate in dichloromethane, Time= 9h, Ambient temperature Subhas Bose; Ravinder Goud; Tetrahedron Letters; vol. 40; nb. 4; (1999); p. 747 - 748 View in Reaxys

84 %

With triethylamine, 2,2,2-Trichloroethyl chloroformate in dichloromethane, T= 0 - 20 °C , Elimination Bose, D. Subhas; Kumar, K. Kiran; Synthetic Communications; vol. 30; nb. 16; (2000); p. 3047 - 3052

12/122

2016-03-14 02:10:57

View in Reaxys 84 %

With triphenylphosphine, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in acetonitrile, Time= 9h, Heating Aghapour, Ghasem; Amirabadi, Marjan; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 46; nb. 4; (2007); p. 649 - 652 View in Reaxys

83 %

With bis(trichloromethyl) carbonate, triethylamine in chloroform, Time= 2h, T= 50 °C Sahu, Devi Prasad; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 32; nb. 3; (1993); p. 385 - 386 View in Reaxys

83 %

With di(n-butyl)tin oxide in toluene, Heating Bose, D. Subhas; Jayalakshmi; Journal of Organic Chemistry; vol. 64; nb. 5; (1999); p. 1713 - 1714 View in Reaxys

83 %

With oxalyl dichloride, Bis-lt;(p-methoxy)phenylgt;cyclopropenon, DBU in dichloromethane, Time= 4.5h, Reflux Rai, Ankita; Yadav, Lal Dhar S.; European Journal of Organic Chemistry; nb. 10; (2013); p. 1889 - 1893 View in Reaxys

81 %

With Ph3PCl(1+)*succinimide(1-), Time= 2h, T= 105 °C Takahashi, Tatsuya; Sugimoto, Osamu; Koshio, Jiro; Tanji, Ken-ichi; Heterocycles; vol. 68; nb. 9; (2006); p. 1973 - 1979 View in Reaxys

81 %

With ((1,3,5-triazine-2,4,6-triyl)tris(oxy))tris(triphenylphosphonium) chloride, Time= 2h, T= 140 - 150 °C Sugimoto, Osamu; Harada, Yukihiro; Tanji, Ken-Ichi; Heterocycles; vol. 86; nb. 2; (2012); p. 1583 - 1590 View in Reaxys

79 %

With pyridine, pivaloyl chloride in dichloromethane, Time= 5.5h, T= 20 °C Venkat Narsaiah; Nagaiah; Advanced Synthesis and Catalysis; vol. 346; nb. 11; (2004); p. 1271 - 1274 View in Reaxys

78 %

With 1,3,5-trichloro-2,4,6-triazine in DMFA, Time= 10h, Ambient temperature Olah, George A.; Narang, Subhash C.; Fung, Alexander P.; Gupta, B.G.Balaram; Synthesis; nb. 8; (1980); p. 657 - 658 View in Reaxys

78 %

With 1,3,5-trichloro-2,4,6-triazine in DMFA, Time= 10h, Ambient temperature, also in dioxan, other temperature, other time, Product distribution Olah, George A.; Narang, Subhash C.; Fung, Alexander P.; Gupta, B.G.Balaram; Synthesis; nb. 8; (1980); p. 657 - 658 View in Reaxys

78 %

With pyridine, 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane, T= 20 °C , Dehydration Bose, D. Subhas; Sunder, K. Sugnana; Synthetic Communications; vol. 29; nb. 23; (1999); p. 4235 - 4239 View in Reaxys

76 %

With di(n-butyl)tin oxide in toluene, Heating, Dehydration Bose, D. Subhas; Jayalakshmi; Goud, P. Ravinder; Synthesis; nb. 10; (1999); p. 1724 - 1726 View in Reaxys

73 %

With N-succinimide chlorotriphenylphosphonium salt, Time= 0.0833333h, microwave irradiation Tanji, Ken-Ichi; Koshio, Jiro; Sugimoto, Osamu; Synthetic Communications; vol. 35; nb. 15; (2005); p. 1983 - 1987 View in Reaxys

13/122

2016-03-14 02:10:57

70 %

With sodium hydroxide, triethylamine in chloroform, Time= 1h, Ambient temperature Schroth, W.; Kluge, H.; Frach, R.; Hodek, W.; Schaedler, H. D.; Journal fuer Praktische Chemie (Leipzig); vol. 325; nb. 5; (1983); p. 787 - 802 View in Reaxys

70 %

With N-chloro-succinimide, triphenylphosphine in dichloromethane, Time= 0.5h, T= 20 °C Iranpoor; Firouzabadi; Aghapour; Synthetic Communications; vol. 32; nb. 16; (2002); p. 2535 - 2541 View in Reaxys

63 %

With trimethylsilylphosphate, Time= 0.25h, Heating Yokoyama, Masataka; Yoshida, Sayaka; Imamoto, Tsuneo; Synthesis; nb. 7; (1982); p. 591 - 592 View in Reaxys

61 %

With (μ3,η2,η3,η5-acenaphthylene)Ru3(CO)7, 1,1,4,4-tetramethyldisilylethylene in DME, Time= 20h, T= 70 °C , Inert atmosphere Hanada, Shiori; Motoyama, Yukihiro; Nagashima, Hideo; European Journal of Organic Chemistry; nb. 24; (2008); p. 4097 - 4100 View in Reaxys

60 %

With 3 A molecular sieve, Time= 0.333333h, T= 225 - 500 °C , p= 0.005Torr , Pyrolysis Campbell, Jacqueline A.; McDougald, Graham; McNab, Hamish; Rees, Lovat V. C.; Tyas, Richard G.; Synthesis; nb. 20; (2007); p. 3179 - 3184 View in Reaxys

54 %

39 %

With trichloroisocyanuric acid, triphenylphosphine in acetonitrile, Time= 3h, Heating Hiegel; Ramirez; Barr; Synthetic Communications; vol. 29; nb. 8; (1999); p. 1415 - 1419 View in Reaxys

38 %

With N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide, copper(l) chloride in toluene, Time= 24h, T= 100 °C Enthaler, Stephan; Weidauer, Maik; Catalysis Letters; vol. 141; nb. 8; (2011); p. 1079 - 1085 View in Reaxys With sodium chloride, phosphoryl chloride Kao; Yen; Chien; Journal of the Chinese Chemical Society (Peking); vol. 2; (1934); p. 240 View in Reaxys With sodium disulfite, phosphoryl chloride Patent; Am. Cyanamid Co.; US2459128; (1946) View in Reaxys With amidosulphuric acid, T= 215 °C Kirsanow; Solotow; Zhurnal Obshchei Khimii; vol. 20; (1950); p. 284,287; ; (1950); p. 6384 View in Reaxys

14/122

2016-03-14 02:10:57

100 % Chromat.

With sodium hydroxide, chloroform, C8H18N2O2, Time= 0.25h, T= 25 °C , further betaine reagents, Product distribution Gold'berg, Yu. Sh.; Abele, E. M.; Kalvin'sh, I. Ya.; Bremanis, G. A.; Shimanskaya, M. V.; Lukevits, E. Ya.; Doklady Chemistry; vol. 294; (1987); p. 295 - 298; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 294; nb. 6; (1987); p. 1387 - 1391 View in Reaxys With thionyl chloride in benzene, Reflux Gao; Zhao; Liu; Shao; Wang; Tang; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 49; nb. 11; (2010); p. 1499 - 1508 View in Reaxys

O N

O NH 2

Rx-ID: 2107194 View in Reaxys 13/395 Yield

Conditions & References

76 %

With sodium bromide in methanol, T= 10 °C , electrooxidation (0.3 A, 75 mA/cm2, 5-7 V) Shono, Tatsuya; Matsumura, Yoshihiro; Inoue, Kenji; Journal of the American Chemical Society; vol. 106; nb. 20; (1984); p. 6075 - 6076 View in Reaxys

C–

Na +

N N N

Rx-ID: 38681956 View in Reaxys 14/395 Yield 69 %

Conditions & References Benzyl nitrile (6) [11] A mixture of benzyloxy benzotriazole 1d (112.6 mg, 0.50 mmol) and NaCN (49 mg, 1.0 mmol) in anhydrous DMSO (1.25 mL) was stirred at 100°C for 1 h. The mixture was diluted with Et2O and washed with a water/brine mixture (1:1), followed by water (3–4x). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. Compound 6 was obtained as a yellow oil (40.2 mg, 69percent yield) without need for additional purification. in dimethyl sulfoxide, Time= 1h, T= 100 °C Lakshman, Mahesh K.; Singh, Manish K.; Kumar, Mukesh; Chamala, Raghu Ram; Yedulla, Vijayender R.; Wagner, Domenick; Leung, Evan; Yang, Lijia; Matin, Asha; Ahmad, Sadia; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 1919 - 1932 View in Reaxys

Rx-ID: 605609 View in Reaxys 15/395 Yield 85 %

Conditions & References With cyanide(1-), lt;Pgt;-(CH2)3-+PBu3 in water, Time= 0.5h, T= 110 °C Chiles, Margaret Shea; Jackson, Donald D.; Reeves, Perry C.; Journal of Organic Chemistry; vol. 45; nb. 14; (1980); p. 2915 - 2918 View in Reaxys With copper (I) cyanide, phenylacetonitrile, copper(l) chloride, T= 160 - 165 °C

15/122

2016-03-14 02:10:57

Patent; Gen. Aniline and Film Corp.; US2195076; (1937) View in Reaxys With phenylacetonitrile, copper(II) sulfate, T= 150 °C Wawzonek; Hsu; Journal of the American Chemical Society; vol. 68; (1946); p. 2741 View in Reaxys With Mg6Al2(OH)16Cl2-xCNx*4H2O (X=1.53-1.94) in toluene, Time= 4h, T= 79.85 °C , Rate constant Suzuki, Eiichi; Inoue, Atsushi; Ono, Yoshio; Chemistry Letters; nb. 12; (1998); p. 1291 - 1292 View in Reaxys 41.20 g (99.0%)

4.ii : (ii) To a solution of 40.00 g (180 mmoles) of benzyl alcohol in 530 ml of dichloromethane was added within 5 min 32.7 ml (450 mmoles) of thionyl chloride. The solution was evaporated in vacuo to dryness, which was repeated after toluene addition: 46.30 g (106.9percent) of crude benzyl chloride, which was dissolved in 230 ml of dimethylformamide and treated with 23.50 g (360 mmoles) of potassium cyanide. The mixture was heated for 4 hours to 50-55° C. The salt was filtered off and the filtrate evaporated in vacuo to dryness, which was repeated after the addition of water, the residue was taken up in ether and extracted with 1N NaOH. The ether phase is evaporated to dryness to yield 41.20 g (99.0percent) of crude benzyl cyanide. With thionyl chloride, benzyl alcohol in N-methylacetamide, dichloromethane, water Patent; Euro-Celtique, S.A.; US6413975; (2002); (B1) English View in Reaxys

41.20 g (99.0%)

4.ii : (ii) To a solution of 40.00 g(180 mmoles) of benzyl alcohol in 530 ml of dichloromethane was added within 5 min 32.7 ml (450 mmoles) of thionyl chloride. The solution was evaporated in vacuo to dryness, which was repeated after toluene addition: 46.30 g (106.9percent) of crude benzyl chloride, which was dissolved in 230 ml of dimethylformamide and treated with 23.50 g (360 mmoles) of potassium cyanide. The mixture was heated for 4 hours to 50-55° C. The salt was filtered off and the filtrate evaporated in vacuo to dryness, which was repeated after the addition of water, the residue was taken up in ether and extracted with 1N NaOH. The ether phase is evaporated to dryness to yield 41.20 g (99.0percent) of crude benzyl cyanide. With thionyl chloride, benzyl alcohol in N-methylacetamide, dichloromethane, water Patent; Euro-Celtique, S.A.; US6319928; (2001); (B1) English View in Reaxys

41.20 g (99.0%)

4.ii : (ii) To a solution of 40.00 g (180 mmoles) of benzyl alcohol in. 530 ml of dichloromethane was added within 5 min 32.7 ml (450 mmoles) of thionyl chloride. The solution was evaporated in vacuo to dryness, which was repeated after toluene addition: 46.30 g (106.9percent) of crude benzyl chloride, which was dissolved in 230 ml of dimethylformamide and treated with 23.50 g (360 mmoles) of potassium cyanide. The mixture was heated for 4 hours to 50-55° C. The salt was filtered off and the filtrate evaporated in vacuo to dryness, which was repeated after the addition of water, the residue was taken up in ether and extracted with 1N NaOL. The ether phase is evaporated to dryness to yield 41.20 g (99.0percent) of crude benzyl cyanide. With thionyl chloride, benzyl alcohol in N-methylacetamide, dichloromethane, water Patent; Euro-Celtique S.A.; US6294541; (2001); (B1) English View in Reaxys

16/122

2016-03-14 02:10:57

O HO

H H 2N

Rx-ID: 2020881 View in Reaxys 16/395 Yield 98 %

Conditions & References With sodium hydroxide, trichloroisocyanuric acid, Time= 0.166667h, T= 25 °C De Luca, Lidia; Giacomelli, Giampaolo; Synlett; nb. 12; (2004); p. 2180 - 2184 View in Reaxys

93 %

With NH4Br in methanol, water, Electrochemical reaction Matthessen, Roman; Claes, Laurens; Fransaer, Jan; Binnemans, Koen; De Vos, Dirk E.; European Journal of Organic Chemistry; vol. 2014; nb. 30; (2014); p. 6649 - 6652 View in Reaxys

80 %

With sodium bromide in methanol, T= 10 °C , electrooxidation (0.3 A, 75 mA/cm2, 5-7 V) 5.7 F/mol Shono, Tatsuya; Matsumura, Yoshihiro; Inoue, Kenji; Journal of the American Chemical Society; vol. 106; nb. 20; (1984); p. 6075 - 6076 View in Reaxys With perchloric acid, N,N-Dichlorobenzenesulfonamide in methanol, water, T= 29.9 °C , other amino acids; var. temp. and conditions; ΔH(excit.), ΔS(excit.), ΔG(excit.), Ea; equilibrium constant, Rate constant, Kinetics, Thermodynamic data Rao, P. Jagan Mohana; Gowda, B. Thimme; Journal of the Indian Chemical Society; vol. 69; nb. 10; (1992); p. 642 - 647 View in Reaxys With hydrochlorid acid, 1E-3M CAT in water, T= 30 °C , other temperatures; dependence on concentrations of acid, oxidant, Cl(-), the solvent composition; E(activ.), ΔS(excit.), ΔH(excit.), ΔG(excit.), Kinetics, Mechanism, Thermodynamic data Mahadevappa, D. S.; Ahmed, M. S.; Gowda, N. M. M.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 19; nb. 4; (1980); p. 325 - 329 View in Reaxys With N-Bromosuccinimide, ammonium chloride in DMFA, Time= 0.333333h, T= 20 °C Laval, Gilles; Golding, Bernard T.; Synlett; nb. 4; (2003); p. 542 - 546 View in Reaxys

89 %Chromat.

With 2HO(1-)*0.04NO3 (1-)*0.14CO3 (2-)*0.64Ni(2+)*0.36Al(3+)*0.02O4W(2-), hydrogen peroxide, NH4Br in water, acetonitrile, T= 20 °C , Reagent/catalyst Claes, Laurens; Matthessen, Roman; Rombouts, Ine; Stassen, Ivo; De Baerdemaeker, Trees; Depla, Diederik; Delcour, Jan A.; Lagrain, Bert; De Vos, Dirk E.; ChemSusChem; vol. 8; nb. 2; (2015); p. 345 - 352 View in Reaxys

S N NH 2

Rx-ID: 3929496 View in Reaxys 17/395 Yield 98 %

Conditions & References With polystyrene-bound diaryl telluroxide in dichloromethane, Time= 1h, Ambient temperature Hu, Nan Xing; Aso, Yoshio; Otsubo, Tetsuo; Ogura, Fumio; Bulletin of the Chemical Society of Japan; vol. 59; nb. 3; (1986); p. 879 - 884 View in Reaxys

95 %

With 1,1'-Thiocarbonyldi-2(1H)-pyridone in toluene, Time= 1.5h, Heating

17/122

2016-03-14 02:10:57

Kim, Sunggak; Yi, Kyu Yang; Journal of Organic Chemistry; vol. 51; nb. 13; (1986); p. 2613 - 2615 View in Reaxys 88 %

With di-2-pyridyl sulfite in dichloromethane, Time= 0.333333h, Ambient temperature Kim, Sunggak; Yi, Kyu Yang; Tetrahedron Letters; vol. 27; nb. 17; (1986); p. 1925 - 1928 View in Reaxys

74 %

With tellurium tetraethoxide in tetrachloromethane, chloroform, Time= 1h, Ambient temperature Omote, Kazushi; Aso, Yoshio; Otsubo, Tetsuo; Ogura, Fumio; Bulletin of the Chemical Society of Japan; vol. 67; nb. 6; (1994); p. 1759 - 1761 View in Reaxys

69 %

With polystyrne-bound selenoxide in ethanol, Time= 24h, Heating Hu, Nan Xing; Aso, Yoshio; Otsubo, Tetsuo; Ogura, Fumio; Chemistry Letters; (1985); p. 603 - 606 View in Reaxys

59 %

With diphosphorous tetraiodide, triethylamine in benzene, Time= 10h, Heating Suzuki, Hitomi; Tani, Hiroyuki; Takeuchi, Setsuko; Bulletin of the Chemical Society of Japan; vol. 58; nb. 8; (1985); p. 2421 - 2422 View in Reaxys

Rx-ID: 437195 View in Reaxys 18/395 Yield 99 %

Conditions & References With indium, sodium lauryl sulfate, Time= 30h, T= 60 °C Park, Leeyoung; Keum, Gyochang; Kang, Soon Bang; Kim, Kwan Soo; Kim, Youseung; Journal of the Chemical Society, Perkin Transactions 1; nb. 24; (2000); p. 4462 - 4463 View in Reaxys

96 %

With sodium hydrogen telluride, acetic acid in ethanol, benzene, Time= 0.333333h, T= -20 °C Blay, Gonzalo; Cardona, Luz; Garcia, Begona; Lahoz, Luisa; Pedro, Jose R.; Tetrahedron; vol. 52; nb. 25; (1996); p. 8611 - 8618 View in Reaxys With ethanol, acetic acid, zinc Hignett; Kay; Journal of the Society of Chemical Industry, London; vol. 54; (1935); p. 98 T View in Reaxys

13C –

K+

Rx-ID: 4571198 View in Reaxys 19/395 Yield

Conditions & References Kinoshita, Takeshi; Tetrahedron Letters; vol. 38; nb. 2; (1997); p. 259 - 262 View in Reaxys 3.1 :A 500 mL round bottom flask is charged with potassium [13]cyanide and tetrabutylammonium bromide. After addition of methylene chloride, water (caution: H13CN evolution possible.) and benzyl bromide, the phase-transfer reaction system is vigorously stirred overnight at room temperature. After this time, the organic phase is carefully separated from the aqueous phase (caution: H13CN evolution possible.) and transferred on a column charged with sodium sulfate for drying. The aqueous phase is extracted with methylene chloride and the organic phase is transferred carefully on the sodium sulfate column. The column is rinsed with methylene chloride and the solvent is carefully removed under reduced pressure at 20° C. to yield crude product, which is purified by chromatography. For chromatographic purifica-

18/122

2016-03-14 02:10:57

tion, crude product is dissolved in methylene chloride and injected on a LiChrosorb.(R). Si 60 column (40-63 μm, size C, 440.x.37 mm, Merck 1.10402) using an ethyl acetate/n-heptane mixture (1:4, v/v) as eluent at a flow rate of 20 mL/ min. and a detection wavelength of 254 nm. The product elutes at these conditions between 25-30 minutes (attention: the product has a UV minimum around 254 nm.). The product fractions are combined and the solvent is carefully removed under reduced pressure at about 20° C. giving an almost colorless oil. With tetrabutylammomium bromide in dichloromethane, water, T= 20 °C Patent; Ly, Tai Wei; US2011/172250; (2011); (A1) English View in Reaxys 4

+ -4K

N N

(v6)

Fe N N

Rx-ID: 31525116 View in Reaxys 20/395 Yield 88 %Chromat.

Conditions & References General experimental procedure for the cyanation of benzyl chlorides General procedure: 0.06 mmol PPh3, 0.02 mmol Pd(OAc)2, and 0.4 mL NMP were added into a dried 20 mL tube under a dry nitrogen atmosphere. After the mixture was stirred at room temperature for about 5 min to give a homogeneous solution, 0.3 mmol K4[Fe(CN)6], 1.5 mmol Na2CO3, 1 mmol benzyl chloride, and 0.4 mL NMP were added under a dry nitrogen atmosphere. The reaction tube was sealed with a septum and placed in a constant-temperature oil bath set at 140(+/-5) °C to perform the reaction for 10 h. Once the reaction time was reached, the mixture was cooled to room temperature, then acetophenone was added as an internal standard. GC analysis of the mixture provided the yield of the product (note: in order to decrease the analysis error, the mixture after the reaction was not purified or concentrated). The cyanation product was purified by column chromatography and identified by 1H NMR, 13C NMR or GC-MS data. With palladium diacetate, sodium carbonate, triphenylphosphine in 1-methyl-pyrrolidin-2-one, Time= 10h, T= 140 °C , Inert atmosphere Ren, Yunlai; Yan, Mengjie; Zhao, Shuang; Sun, Yanpei; Wang, Jianji; Yin, Weiping; Liu, Zhifei; Tetrahedron Letters; vol. 52; nb. 39; (2011); p. 5107 - 5109 View in Reaxys

78 %Chromat.

General experimental procedure for cyanation of benzyl chlorides General procedure: 0.3 mmol CuI and 0.3 mL toluene were added into a dried 40 mL tube under a dry nitrogen atmosphere. After the mixture was stirred at room temperature for about 1 min, 0.5 mmol K4[Fe(CN)6], 1 mmol benzyl chloride, and 0.7 mL toluene were added under a dry nitrogen atmosphere. The reaction tube was sealed with a septum and placed in a constant-temperature oil bath set at 180(+/-5) °C to perform the reaction for 20 h. Once the reaction time was reached, the mixture was cooled to room temperature, then 1 mL solution of acetophenone (0.8 mmol/mL in dichloromethane) was added as an internal standard into the reaction tube. Subsequently, GC analysis of the mixture provided the yield of the product (note: in order to decrease the analysis error, the mixture after the reaction was not purified or concentrated). The cyanation product was identified by GC-MS data. With copper(l) iodide in toluene, Time= 20h, T= 180 °C , Inert atmosphere, Sealed tube Ren, Yunlai; Dong, Chuanhua; Zhao, Shuang; Sun, Yanpei; Wang, Jianji; Ma, Junying; Hou, Chaodong; Tetrahedron Letters; vol. 53; nb. 23; (2012); p. 2825 - 2827 View in Reaxys

Rx-ID: 605261 View in Reaxys 21/395 Yield 97 %

Conditions & References With potassium carbonate, 18-C-6-AN in acetonitrile, Time= 5h, Heating, other catalysts, solvents, bases

19/122

2016-03-14 02:10:57

Shapiro, E. A.; Pereverzeva, Yu. O.; Nefedov, A. O.; Eismont, M. Yu.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 38; nb. 11.2; (1989); p. 2432 - 2433; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 11; (1989); p. 2647 - 2648 View in Reaxys 92 %

With N,N,N',N'-tetramethylguanidine in acetonitrile Dowd; Wilk; Wlostowski; Synthetic Communications; vol. 23; nb. 16; (1993); p. 2323 - 2329 View in Reaxys With potassium hydroxide Nasarow et al.; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1957); p. 976,978; engl. Ausg. S. 1000, 1002 View in Reaxys With lithium hydride, 1.) THF, room temperature, 1 h, 2.) THF, reflux, 2 h, Yield given. Multistep reaction Tsuruoka, Akihiko; Negi, Shigeto; Yanagisawa, Manabu; Nara, Kazumasa; Naito, Toshihiko; Minami, Norio; Synthetic Communications; vol. 27; nb. 20; (1997); p. 3547 - 3557 View in Reaxys

I N N

Rx-ID: 37685453 View in Reaxys 22/395 Yield

Conditions & References General Procedure for the One-Pot Synthesis of Primary Thioamides 3 General procedure: A mixture of aldehyde 1 (1.5 mmol) and iodine (1.6 mmol) in ammonia water (10 mL of 28percent solution) was stirred at room temperature for 30 min. The dark reaction mixture fainted in colour at the end of reaction. The excess of ammonia was removed by stirring at 90 °C. Then, O,O-diethyl dithiophosphoric acid (2) (1.5 mmol) was added and the reaction mixture was stirred at 90 °C for 2-4 h (Table 2). After completion of the reaction (monitored by TLC), the mixture was cooled to r.t. The product thus precipitated was filtered, washed with aqueous sodium thiosulfate solution followed by water and dried under reduced pressure to give pure primary thioamides 3 (Table 2). With ammonia in water, T= 20 °C , Green chemistry Yadav, Arvind K.; Srivastava, Vishnu P.; Yadav, Lal Dhar S.; Synthetic Communications; vol. 44; nb. 3; (2014); p. 408 - 416 View in Reaxys

N Cl

B HO

Rx-ID: 40599763 View in Reaxys 23/395 Yield

Conditions & References

85 %

With dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine, palladium diacetate, sodium carbonate in 1,4-dioxane, water, Time= 12h, T= 60 °C , Inert atmosphere, Sealed tube, Reagent/catalyst, Temperature, Concentration Nambo, Masakazu; Yar, Muhammad; Smith, Joel D.; Crudden, Cathleen M.; Organic Letters; vol. 17; nb. 1; (2015); p. 50 - 53 View in Reaxys

N Br H

O B O

B O

Rx-ID: 8680224 View in Reaxys 24/395

20/122

2016-03-14 02:10:57

Yield

Conditions & References

59 %, 20 % With triethylamine, 2-dicyclohexylphosphino-1,1'-biphenyl, palladium diacetate in diethyl ether, Time= 1h, T= 80 °C Baudoin; Guenard; Gueritte; Journal of Organic Chemistry; vol. 65; nb. 26; (2000); p. 9268 - 9271 View in Reaxys

N Cl

Rx-ID: 9745631 View in Reaxys 25/395 Yield

Conditions & References

90 %

With TEA in dichloromethane, Time= 2h, T= 25 °C De Luca, Lidia; Giacomelli, Giampaolo; Synlett; nb. 12; (2004); p. 2180 - 2184 View in Reaxys

90 %

With triethylamine in dichloromethane, Time= 2h, T= 25 °C Ghorbani-Vaghei, Ramin; Veisi, Hojat; Synthesis; nb. 6; (2009); p. 945 - 950; Art.No: Z23008ST View in Reaxys

Rx-ID: 2396901 View in Reaxys 26/395 Yield 100 %

Conditions & References With Sucrose-ethyleneoxide adducts in acetonitrile, Time= 8h, T= 20 °C , further catalysts: PEG, DB18K6; further objects of study: phase-transfer catalysis; further solvents: toluene/H2O, Product distribution Gruber, Heinrich; Greber, Gerd; Monatshefte fuer Chemie; vol. 112; (1981); p. 1063 - 1076 View in Reaxys

97 %

With water, Aliquatreg; 336, Time= 2h, Ambient temperature Bram, G.; Loupy, A.; Pedoussaut, M.; Bulletin de la Societe Chimique de France; nb. 1; (1986); p. 124 - 128 View in Reaxys

97 %

With poly(ethylene glycol)-supported tetrabutylamminium bromide in water, Time= 2h, T= 25 °C , Substitution Annunziata, Rita; Benaglia, Maurizio; Cinquini, Mauro; Cozzi, Franco; Tocco, Graziella; Organic Letters; vol. 2; nb. 12; (2000); p. 1737 - 1739 View in Reaxys

92 %

With 1-n-butyl-3-methylimidazolium hexafluorophosphate in water, Time= 16h, T= 25 °C Lourenco, Nuno M.T.; Afonso, Carlos A.M.; Tetrahedron; vol. 59; nb. 6; (2003); p. 789 - 794 View in Reaxys

78 %

With aluminum oxide in toluene, Time= 10h, T= 50 °C , Irradiation, ultrasound Ando, Takashi; Kawate, Takehiko; Ichihara, Junko (nee Yamawaki); Hanafusa, Terukiyo; Chemistry Letters; (1984); p. 725 - 728 View in Reaxys

71 %

With aluminum oxide in toluene, Time= 24h, T= 50 °C , Irradiation, ultrasonication, change of reaction pathway, var. of solvent, Product distribution Ando, Takashi; Sumi, Shinjiro; Kawate, Takehiko; Ichihara, Junko; Hanafusa, Terukiyo; Journal of the Chemical Society, Chemical Communications; nb. 7; (1984); p. 439 - 440 View in Reaxys

71 %

With aluminum oxide in toluene, Time= 24h, T= 50 °C , Irradiation, ultrasonication

21/122

2016-03-14 02:10:57

Ando, Takashi; Sumi, Shinjiro; Kawate, Takehiko; Ichihara, Junko; Hanafusa, Terukiyo; Journal of the Chemical Society, Chemical Communications; nb. 7; (1984); p. 439 - 440 View in Reaxys With cross-linked polystyrene resin in water, toluene, T= 90 °C , initial rate of the reaction, other temperature and catalysts, variation of benzyl bromide concentrations, Equilibrium constant Takeuchi, Hirofumi; Kikuchi, Masahiro; Miwa, Yoshihisa; Okada, Yutaro; Chemical & Pharmaceutical Bulletin; vol. 30; nb. 11; (1982); p. 3865 - 3871 View in Reaxys With immobilized phase transfer catalyst in water, toluene, T= 70 °C Takeuchi, Hirofumi; Miwa, Yoshihisa; Morita, Shushi; Okada, Jutaro; Chemical & Pharmaceutical Bulletin; vol. <3> 32; (1984); p. 823 - 831 View in Reaxys With hemin copolymer 1, 1.) water, 12 h, 2.) benzene, 10 h, 60 deg C, Yield given. Multistep reaction Saito, Kiyoshi; Harada, Kaoru; Bulletin of the Chemical Society of Japan; vol. 62; nb. 8; (1989); p. 2562 - 2566 View in Reaxys Nabil Aboul-Enein; El-Azzounya; Maklad; Attia; Wiese; Scientia Pharmaceutica; vol. 69; nb. 4; (2001); p. 329 - 350 View in Reaxys With polycationic aryl ether dendrimer in dichloromethane, water, T= 20 °C Kleij, Arjan W.; Coevering, Rob van de; Gebbink, Robertus J. M. Klein; Noordman, Anne-Marie; Spek, Anthony L.; Koten, Gerard van; Chemistry--A European Journal; vol. 7; nb. 1; (2001); p. 181 - 192 View in Reaxys

HO N NH 2

NH 2

Rx-ID: 8811249 View in Reaxys 27/395 Yield

Conditions & References

88 %, 10 % With tetraethylammonium bromide, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in acetonitrile, Time= 0.5h, T= 20 °C Deshmukh, Swapnil S.; Huddar, Sameerana N.; Bhalerao, Dinesh S.; Akamanchi, Krishnacharya G.; Arkivoc; vol. 2010; nb. 2; (2010); p. 118 - 126 View in Reaxys 81 %, 10 % With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in water, acetonitrile, Time= 0.5h, T= 20 °C Deshmukh, Swapnil S.; Huddar, Sameerana N.; Bhalerao, Dinesh S.; Akamanchi, Krishnacharya G.; Arkivoc; vol. 2010; nb. 2; (2010); p. 118 - 126 View in Reaxys 77 %, 18 % With oxygen, sodium methylate in methanol, T= 20 °C , Irradiation Oecal, Nueket; Erden, Ihsan; Tetrahedron Letters; vol. 42; nb. 29; (2001); p. 4765 - 4767 View in Reaxys

C–

Si O

N+

Rx-ID: 9648659 View in Reaxys 28/395 Yield 95 %

Conditions & References With triphenylphosphine, 2,3-dicyano-5,6-dichloro-p-benzoquinone in acetonitrile, Time= 0.0833333h, T= 20 °C

22/122

2016-03-14 02:10:57

Iranpoor, Nasser; Firouzabadi, Habib; Akhlaghinia, Batool; Nowrouzi, Najmeh; Journal of Organic Chemistry; vol. 69; nb. 7; (2004); p. 2562 - 2564 View in Reaxys

C–

N N+

Rx-ID: 9672007 View in Reaxys 29/395 Yield

Conditions & References

96 %

With triphenylphosphine, 2,3-dicyano-5,6-dichloro-p-benzoquinone in acetonitrile, Time= 0.0833333h, T= 20 °C Iranpoor, Nasser; Firouzabadi, Habib; Akhlaghinia, Batool; Nowrouzi, Najmeh; Journal of Organic Chemistry; vol. 69; nb. 7; (2004); p. 2562 - 2564 View in Reaxys

C–

N N+

Rx-ID: 9681939 View in Reaxys 30/395 Yield

Conditions & References

94 %

With triphenylphosphine, 2,3-dicyano-5,6-dichloro-p-benzoquinone in acetonitrile, T= 20 °C Iranpoor, Nasser; Firouzabadi, Habib; Akhlaghinia, Batool; Nowrouzi, Najmeh; Journal of Organic Chemistry; vol. 69; nb. 7; (2004); p. 2562 - 2564 View in Reaxys

N N

H 2N

Rx-ID: 35423759 View in Reaxys 31/395 Yield

Conditions & References Cu(I)/TEMPO-Catalyzed Aerobic Oxidation of Primary Amines to Imines General procedure: The mixture of benzylamine 1a (5.0 mmol), CuI (0.0190 g, 0.1 mmol, 2 molpercent), and TEMPO (0.0156 g, 0.1 mmol, 2 molpercent) was directly stirred in open air at room temperature (ca. 30 oC) in a reaction tube. After completion of the reaction as monitored by GC-MS and/or TLC, the mixture was then directly purified, without any workup, through a Et3N-washed silica gel column using ethyl acetate and petroleum ether as the eluent, affording Nbenzylidenebenzylamine 2a in 85percent isolated yield. With 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical, copper(l) chloride in neat (no solvent), Time= 48h, T= 60 °C Huang, Bo; Tian, Haiwen; Lin, Shoushuai; Xie, Meihua; Yu, Xiaochun; Xu, Qing; Tetrahedron Letters; vol. 54; nb. 22; (2013); p. 2861 - 2864 View in Reaxys

Rx-ID: 604995 View in Reaxys 32/395 Yield 94 %

Conditions & References With PEG400, Time= 8h, T= 120 °C Cao; Chen; Pei; Synthetic Communications; vol. 31; nb. 14; (2001); p. 2203 - 2207

23/122

2016-03-14 02:10:57

View in Reaxys With water, T= 110 - 115 °C Gomberg; Buchler; Journal of the American Chemical Society; vol. 42; (1920); p. 2067 View in Reaxys With ethanol Leonard; Journal of the American Chemical Society; vol. 47; (1925); p. 1778 View in Reaxys With acetone, sodium iodide Patent; Knoll A.G.; US2734908; (1951) View in Reaxys With N,N-dimethyl-cyclohexylamine, chlorobenzene Patent; Monsanto Chem. Co.; US2783265; (1954) View in Reaxys Organic Syntheses 2; View in Reaxys With poly(styrene-co-chloromethylstyrene), trimethylamine in water, toluene, T= 90 °C , influence of particle size and percent of divinylbenzene, Rate constant Tomoi, M.; Ford, Warren T.; Journal of the American Chemical Society; vol. 103; nb. 13; (1981); p. 3828 - 3832 View in Reaxys With tetrabutylammomium bromide in ethanol, water, Time= 6.5h, Heating Shackleford, David M.; Hayball, Peter J.; Reynolds, Geoffrey D.; Hamon, David P. G.; Evans, Allan M.; Milne, Robert W.; Nation, Roger L.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 44; nb. 3; (2001); p. 225 - 234 View in Reaxys With sodium hydroxide, N,N-didecyl-N,N-dimethylammonium bromide in toluene, Time= 1h, T= 105 °C Chidambaram, Mandan; Sonavane, Sachin U.; de la Zerda, Jaima; Sasson, Yoel; Tetrahedron; vol. 63; nb. 32; (2007); p. 7696 - 7701 View in Reaxys 99.0 7 :In Example 7, benzyl cyanide was prepared by dissolving sodium cyanide (20 mmoles = 0.98 g) in water (100 g) in %Chromat. a three neck flask of 250 mL. The reaction flask was immersed in the water bath at 50°C and stirred mechanically (about 500 rpm). Then, a mixture consisting of benzyl chloride (60 mmoles = 7.60 g), Aliquat 336 (2 mmoles = 0.88 g), and sodium iodide (3 mmoles = 0.45g) was added to the water phase. The reaction mixture was stirred mechanically at 50°C. The major product is benzyl cyanide in the organic phase and was obtained at a 99.0percent theoretical yield based on limiting reactant sodium cyanide after 135 minutes. Analysis was done with an external standard of Durene (tetramethylbenzene) on a Gas Chromatograph. With Aliquatreg; 336, sodium iodide in water, Time= 2.25h, T= 50 °C Patent; VALUE RECOVERY, INC.; WO2003/74448; (2003); (A2) English View in Reaxys Br

Rx-ID: 8677944 View in Reaxys 33/395 Yield 99 %

Conditions & References With indium, sodium lauryl sulfate, Time= 6h, T= 20 °C

24/122

2016-03-14 02:10:57

Park, Leeyoung; Keum, Gyochang; Kang, Soon Bang; Kim, Kwan Soo; Kim, Youseung; Journal of the Chemical Society, Perkin Transactions 1; nb. 24; (2000); p. 4462 - 4463 View in Reaxys 87.1 %

With indium, acetic acid in methanol, Time= 1h, T= 20 °C Lee, Seung Hwan; Cho, Min Young; Nam, Mi Hye; Park, Young Sang; Yoo, Byung Woo; Lee, Chi-Woo; Yoon, Cheol Min; Synthetic Communications; vol. 35; nb. 10; (2005); p. 1335 - 1341 View in Reaxys

N I O

B O

Rx-ID: 8680726 View in Reaxys 34/395 Yield

Conditions & References

90 %, 10 % With triethylamine, 2-dicyclohexylphosphino-1,1'-biphenyl, palladium diacetate, Time= 0.5h, T= 80 °C Baudoin; Guenard; Gueritte; Journal of Organic Chemistry; vol. 65; nb. 26; (2000); p. 9268 - 9271 View in Reaxys

Rx-ID: 32651540 View in Reaxys 35/395 Yield

Conditions & References With potassium fluoride, [Pd(η3-2-Me-C3H4)(μ-Cl)]2 in N,N-dimethyl-formamide, Time= 12h, T= 80 °C , p= 7600.51Torr

20 %

Park, Ahbyeol; Lee, Sunwoo; Organic Letters; vol. 14; nb. 4; (2012); p. 1118 - 1121 View in Reaxys

Br 2H

Rx-ID: 1993501 View in Reaxys 36/395 Yield 61 %

Conditions & References in ethylene glycol, T= 110 °C Wierlacher, Stefan; Sander, Wolfram; Uu, Michael T. H.; Journal of the American Chemical Society; vol. 115; nb. 20; (1993); p. 8943 - 8953 View in Reaxys

O N

Rx-ID: 2062733 View in Reaxys 37/395 Yield 71 %

Conditions & References With trimethylsilyl iodide in dichloromethane, Time= 16h, T= 25 °C Olah, George A.; Narang, Subhash C.; Field, Leslie D.; Fung, Alexander P.; Journal of Organic Chemistry; vol. 48; nb. 16; (1983); p. 2766 - 2767 View in Reaxys

25/122

2016-03-14 02:10:57

13C

N 13C

Rx-ID: 2695333 View in Reaxys 38/395 Yield

Conditions & References

90.3 %

With 18-crown-6 ether in acetonitrile, Time= 12h, T= 18 °C Cox, Russell J.; O'Hagan, David; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 10; (1991); p. 2537 - 2540 View in Reaxys Bertha, Ferenc; Fetter, Jozsef; Lempert, Karoly; Kajtar-Peredy, Maria; Czira, Gabor; Koltai, Erno; Tetrahedron; vol. 57; nb. 42; (2001); p. 8889 - 8895 View in Reaxys O

N N

Rx-ID: 10235291 View in Reaxys 39/395 Yield

Conditions & References

45 %, 36 % With pyridinium chlorochromate in dichloromethane, T= 0 - 20 °C Fan, Qiu-Hua; Ni, Nan-Ting; Li, Qin; Zhang, Li-He; Ye, Xin-Shan; Organic Letters; vol. 8; nb. 5; (2006); p. 1007 1009 View in Reaxys

N O

Rx-ID: 26035708 View in Reaxys 40/395 Yield

Conditions & References

89 %, 80 % With 2,2'-azo-bisisobutyronitrile, tri-n-butyl-tin hydride in benzene, T= 80 °C Bencivenni, Giorgio; Lanza, Tommaso; Leardini, Rino; Minozzi, Matteo; Nanni, Daniele; Spagnolo, Piero; Zanardi, Giuseppe; Journal of Organic Chemistry; vol. 73; nb. 12; (2008); p. 4721 - 4724 View in Reaxys

Rx-ID: 3838806 View in Reaxys 41/395 Yield 98 %

Conditions & References With chloro-trimethyl-silane, sodium iodide in N,N-dimethyl-formamide, acetonitrile, Time= 2h, T= 60 - 65 °C Davis, Roman; Untch, Karl G.; Journal of Organic Chemistry; vol. 46; nb. 14; (1981); p. 2985 - 2987 View in Reaxys

94 %

With triethylamine, tetra-(n-butyl)ammonium iodide in N,N-dimethyl-formamide, Time= 3h, Heating, Product distribution, Further Variations: Catalysts, Reagents, Solvents Soltani Rad, Mohammad Navid; Khalafi-Nezhad, Ali; Behrouz, Somayeh; Faghihi, Mohammad Ali; Tetrahedron Letters; vol. 48; nb. 38; (2007); p. 6779 - 6784 View in Reaxys

26/122

2016-03-14 02:10:57

NZ N

NH 2

Rx-ID: 9375695 View in Reaxys 42/395 Yield

Conditions & References

70 %

With potassium hydroxide in methanol, T= 15 °C , Electrochemical reaction Okimoto, Mitsuhiro; Takahashi, Yukio; Bulletin of the Chemical Society of Japan; vol. 76; nb. 2; (2003); p. 427 - 428 View in Reaxys

N O

P O

Rx-ID: 9777212 View in Reaxys 43/395 Yield

Conditions & References

82 %

With 2,6-dimethyl-1,4-benzoquinone in chloroform, Time= 24h, T= 20 °C Masutani, Kouta; Minowa, Tomofumi; Hagiwara, Yoshiaki; Mukaiyama, Teruaki; Bulletin of the Chemical Society of Japan; vol. 79; nb. 7; (2006); p. 1106 - 1117 View in Reaxys

82 % Spectr.

With 2,6-dimethyl-1,4-benzoquinone in chloroform, Time= 24h, T= 20 °C Mukaiyama, Teruaki; Masutani, Kouta; Hagiwara, Yoshiaki; Chemistry Letters; vol. 33; nb. 9; (2004); p. 1192 - 1193 View in Reaxys N

Cl O

O O

Rx-ID: 24363393 View in Reaxys 44/395 Yield 51%

Conditions & References 21.B : B. B. 2,6-bis-[3,4-(methylenedioxy)phenoxy]benzyl cyanide Sodium cyanide (85 mg, 1.6 mmol) was added to a solution of 2,6-bis-[(3,4-(methylenedioxy)phenoxy]-benzyl chloride (435 mg, 1.1 mmol) in DMF (3 ml) at room temperature. The resulting dark brown solution was stirred at room temperature for 18 hours. The DMF was removed under high vacuum and the remaining brown residue was extracted into ethyl acetate and washed with brine (1*5 ml). After drying over MgSO4, the solvent was removed by evaporation and the remaining solid was purified by column chromatography using 10percent ethyl acetate-hexanes which yielded 217 mg (51percent yield) of the pure benzyl cyanide as a white powder. in N,N-dimethyl-formamide Patent; Texas Biotechnology Corporation; US5977117; (1999); (A1) English View in Reaxys

27/122

2016-03-14 02:10:57

+ -4K

N N

(v6)

N N

Rx-ID: 31525117 View in Reaxys 45/395 Yield

Conditions & References

41 %Chro- With palladium diacetate, sodium carbonate in 1-methyl-pyrrolidin-2-one, Time= 10h, T= 140 °C , Inert atmosphere mat., 8 %Chromat. Ren, Yunlai; Yan, Mengjie; Zhao, Shuang; Sun, Yanpei; Wang, Jianji; Yin, Weiping; Liu, Zhifei; Tetrahedron Letters; vol. 52; nb. 39; (2011); p. 5107 - 5109 View in Reaxys 30 %Chromat.

2.2 General procedure for the reactions in Table S3 General procedure: 0.3 mmol CuI and 0.3 mL solvent were added into a dried 40 mL tube under a dry nitrogen atmosphere. After the mixture was stirred at room temperature for about 1 min, 0.5 mmol K4[Fe(CN)6], 1 mmol benzyl chloride, and 0.7 mL solvent were added under a dry nitrogen atmosphere. The reaction tube was sealed with a septum and placed in a constant-temperature oil bath set at 180(+/-5) oC to perform the reaction for 20 h. For an analysis of the product see the general procedure for the reactions in Table S2. With copper(l) iodide, water, Time= 20h, T= 180 °C , Inert atmosphere, Sealed tube Ren, Yunlai; Dong, Chuanhua; Zhao, Shuang; Sun, Yanpei; Wang, Jianji; Ma, Junying; Hou, Chaodong; Tetrahedron Letters; vol. 53; nb. 23; (2012); p. 2825 - 2827 View in Reaxys

cyanide ion

Rx-ID: 35908873 View in Reaxys 46/395 Yield

Conditions & References

100 %

With highly branchedpolyacrylamide-APTMAI in water, toluene, Time= 0.5h, T= 20 - 70 °C Mahdavi, Hossein; Amirsadeghi, Mehdi; Journal of the Iranian Chemical Society; vol. 10; nb. 4; (2013); p. 791 - 797 View in Reaxys

Rx-ID: 40499695 View in Reaxys 47/395 Yield

Conditions & References

85 %

With sodium azide, palladium diacetate, 2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl in acetone, Time= 8h, T= 80 °C , Inert atmosphere Zou, Tao; Yu, Xiaoqiang; Feng, Xiujuan; Bao, Ming; Chemical Communications; vol. 51; nb. 53; (2015); p. 10714 10717 View in Reaxys H

13C 2

H 13 2 C

Rx-ID: 2257214 View in Reaxys 48/395 Yield 90 %

Conditions & References in ethanol Apeloig, Yitzhak; Franke, Wilfried; Rappoport, Zvi; Schwarz, Helmut; Stahl, Daniel; Journal of the American Chemical Society; vol. 103; nb. 10; (1981); p. 2770 - 2780 View in Reaxys

28/122

2016-03-14 02:10:57

O S

O N HO

Rx-ID: 2570434 View in Reaxys 49/395 Yield

Conditions & References

85 %

With titanium(III) chloride in tetrahydrofuran, Time= 4h Wade, Peter A.; Hinney, Harry R.; Amin, Nayan V.; Vail, Peter D.; Morrow, Scott D.; et al.; Journal of Organic Chemistry; vol. 46; (1981); p. 765 - 770 View in Reaxys

N O

Rx-ID: 3949104 View in Reaxys 50/395 Yield

Conditions & References

69 %, 15 % With titanium tetrachloride, zinc in tetrahydrofuran, dichloromethane, Time= 3h, T= -15 °C Uno, Hidemitsu; Fujiki, Satomi; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 59; nb. 4; (1986); p. 1267 - 1268 View in Reaxys 15 %, 69 % With titanium tetrachloride, zinc in tetrahydrofuran, dichloromethane, Time= 3h, T= -15 °C Uno, Hidemitsu; Fujiki, Satomi; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 59; nb. 4; (1986); p. 1267 - 1268 View in Reaxys

15N

Rx-ID: 8688371 View in Reaxys 51/395 Yield

Conditions & References

91 %

With tributyl-amine in water, Time= 3h, T= 100 - 105 °C , Condensation Rykowski; Wolinska; Van Der Plas; Journal of Heterocyclic Chemistry; vol. 37; nb. 4; (2000); p. 879 - 883 View in Reaxys

O–

F N

F F

I+

Rx-ID: 10438494 View in Reaxys 52/395 Yield 99 %

Conditions & References Stage 1: With n-butyllithium in tetrahydrofuran, Time= 0.25h, T= -78 °C Stage 2: With tetrabutyl ammonium fluoride in tetrahydrofuran, Time= 0.916667h, T= 0 - 20 °C Kamila, Sukanta; Koh, Benjamin; Biehl, Edward R.; Synthetic Communications; vol. 36; nb. 23; (2006); p. 3493 3507 View in Reaxys

29/122

2016-03-14 02:10:57

N Cl O

O N O

Rx-ID: 22873156 View in Reaxys 53/395 Yield

Conditions & References

9.2 g (53%) X : PREPARATION X, 3-(Indan-2-yloxy)-4-Methoxybenzyl Cyanide PREPARATION X 3-(Indan-2-yloxy)-4-Methoxybenzyl Cyanide 3-(Indan-2-yloxy)-4-methoxybenzyl chloride (17.7 g, 61.4 mmol) is dissolved in 150 ml dimethylsulfoxide and is treated with potassium cyanide (7.9 g, 121.5 mmol). The reaction is stirred at room temperature for 4.5 hours then partitioned between water and ethyl acetate. It is washed 2 x H2, 2 x brine, dried over MgSO4 filtered and concentrated in vacuo . The crude material is purified by flash chromatography (SiO2 3:1 hexane/ethyl acetate). The appropriate fractions are combined and concentrated in vacuo to afford 9.2 g (53percent) of the benzyl cyanide as a pale yellow solid. With potassium cyanide in dimethyl sulfoxide Patent; PFIZER INC.; EP247725; (1994); (B1) english View in Reaxys

O N

+ N Na

O–

Rx-ID: 30891821 View in Reaxys 54/395 Yield

Conditions & References

87 %

With dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine, bis(η3-allyl-μ-chloropalladium(II)) in 1,3,5-trimethyl-benzene, Time= 5.16667h, T= 20 - 140 °C , Inert atmosphere, Sealed tube, chemoselective reaction Shang, Rui; Ji, Dong-Sheng; Chu, Ling; Fu, Yao; Liu, Lei; Angewandte Chemie - International Edition; vol. 50; nb. 19; (2011); p. 4470 - 4474 View in Reaxys

O O

Na +

S O

–

Rx-ID: 33097286 View in Reaxys 55/395 Yield 76 %

Conditions & References With pyridine, hydroxylamine hydrochloride in toluene, Time= 11h, T= 80 °C , Reflux Zhu, Jintao; Song, Guangwei; Yao, Guoxin; Chen, Gang; Synthetic Communications; vol. 42; nb. 13; (2012); p. 1934 - 1940 View in Reaxys

Rx-ID: 1710695 View in Reaxys 56/395 Yield 72 %

Conditions & References With bis (triortho-tolylphosphine)palladium(II) chloride in m-xylene, Time= 3h, T= 120 °C , var. cat.: PdCl2(PPh3)2, var. solv. and temp. Kosugi, Masanori; Ishiguro, Masahiro; Negishi, Yoshikazu; Sano, Hiroshi; Migita, Toshihiko; Chemistry Letters; (1984); p. 1511 - 1512

30/122

2016-03-14 02:10:57

View in Reaxys

Rx-ID: 2013382 View in Reaxys 57/395 Yield

Conditions & References

99 %

Stage 1: With 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical, 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione in dichloromethane, Time= 0.5h, T= 0 - 20 °C , Inert atmosphere Stage 2: With ammonia, iodine in dichloromethane, water, Time= 2h, T= 20 °C , Inert atmosphere Shimojo, Hiroyuki; Moriyama, Katsuhiko; Togo, Hideo; Synthesis (Germany); vol. 45; nb. 15; (2013); p. 2155 2164; Art.No: SS-2013-F0311-OP View in Reaxys

90 %

With TCBDA, ammonia in water, T= 25 - 60 °C Ghorbani-Vaghei, Ramin; Veisi, Hojat; Synthesis; nb. 6; (2009); p. 945 - 950; Art.No: Z23008ST View in Reaxys

87 %

With 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical, (hydroxy(tosyloxy)iodo)benzene, ammonium acetate in water, acetonitrile, Time= 4h, T= 80 °C Zhu, Chenjie; Sun, Chengguo; Wei, Yunyang; Synthesis; nb. 24; (2010); p. 4235 - 4241; Art.No: F14610SS View in Reaxys

80 %

With trichloroisocyanuric acid, ammonia in water, T= 20 - 60 °C Veisi, Hojat; Synthesis; nb. 15; (2010); p. 2631 - 2635; Art.No: Z04110SS View in Reaxys

80 %

With Iron (III) nitrate nonahydrate, ammonium hydroxide, 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical in acetonitrile, Time= 12h, T= 20 °C Dighe, Shashikant U.; Chowdhury, Deepan; Batra, Sanjay; Advanced Synthesis and Catalysis; vol. 356; nb. 18; (2014); p. 3892 - 3896 View in Reaxys With ammonia, silica gel, nickel, copper, T= 300 °C , vapor-phase synthesis; var. partial pressure of reactents, Yield given Takeuchi; Miwa; Okada; Chemical and Pharmaceutical Bulletin; vol. 28; nb. 9; (1980); p. 2637 - 2641 View in Reaxys With ammonia, silica gel, nickel, copper, T= 300 °C , vapor-phase,var. partial press. of reactants, Rate constant Takeuchi; Miwa; Okada; Chemical and Pharmaceutical Bulletin; vol. 28; nb. 9; (1980); p. 2637 - 2641 View in Reaxys With ammonium hydroxide, sodium periodate, potassium iodide, Time= 3h, T= 60 °C Zolfigol, Mohammad Ali; Hajjami, Maryam; Ghorbani-Choghamarani, Arash; Bulletin of the Korean Chemical Society; vol. 32; nb. 12; (2011); p. 4191 - 4194 View in Reaxys

Rx-ID: 2395345 View in Reaxys 58/395 Yield 94 %

Conditions & References With 1-methyl-2-(methylsulfinyl)pyridine in water, Time= 1h, T= 100 °C , variation of amounts of catalyst, temperatures and solvents

31/122

2016-03-14 02:10:57

Furukawa, Naomichi; Kishimoto, Keiko; Ogawa, Satoshi; Kawai, Tsutomu; Fujihara, Hisashi; Oae, Shigeru; Tetrahedron Letters; vol. 22; nb. 44; (1981); p. 4409 - 4412 View in Reaxys 94 %

With 1-methyl-2-(methylsulfinyl)pyridine in water, Time= 1h, T= 100 °C Furukawa, Naomichi; Kishimoto, Keiko; Ogawa, Satoshi; Kawai, Tsutomu; Fujihara, Hisashi; Oae, Shigeru; Tetrahedron Letters; vol. 22; nb. 44; (1981); p. 4409 - 4412 View in Reaxys With poly(styrene-co-chloromethylstyrene), trimethylamine in water, toluene, T= 90 °C , influence of particle size and degree of cross-linking on activation parameters, further catalysts (tri-n-butylphosphine); influence of mechanical stiiring speed, Thermodynamic data, Rate constant Tomoi, M.; Ford, Warren T.; Journal of the American Chemical Society; vol. 103; nb. 13; (1981); p. 3828 - 3832 View in Reaxys

85 % Chro- With -(1-MeO-4-CH2NMe3Cl-C6H2-(CH2)-2-yl-6)6 in water, Time= 2h, T= 60 °C mat. Shimizu, Shoichi; Kito, Katsuyuki; Sasaki, Yasuyuki; Hirai, Choichiro; Chemical Communications; nb. 17; (1997); p. 1629 - 1630 View in Reaxys in ethanol, water, Time= 4h, Heating Law, Ho; Dukat, Malgorzata; Teitler, Milt; Lee, David K. H.; Mazzocco, Lucia; Kamboj, Raj; Rampersad, Vik; Prisinzano, Thomas; Glennon, Richard A.; Journal of Medicinal Chemistry; vol. 41; nb. 13; (1998); p. 2243 - 2251 View in Reaxys

N S

Rx-ID: 2536532 View in Reaxys 59/395 Yield

Conditions & References

98 %

With acetic acid, zinc, Time= 1h, T= 100 °C Tamura, Yasumitsu; Choi, Hong Dae; Mizutani, Masako; Ueda, Yuko; Ishibashi, Hiroyuki; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 10; (1982); p. 3574 - 3579 View in Reaxys With zinc in acetic acid, Time= 1h, T= 100 °C Tamura; Shindo; Uenishi; Ishibashi; Tetrahedron Letters; vol. 21; nb. 26; (1980); p. 2547 - 2548 View in Reaxys

N O

O O

Rx-ID: 2664976 View in Reaxys 60/395 Yield 74 %

Conditions & References With titanium(III) chloride in tetrahydrofuran, Time= 4h Wade, Peter A.; Hinney, Harry R.; Amin, Nayan V.; Vail, Peter D.; Morrow, Scott D.; et al.; Journal of Organic Chemistry; vol. 46; (1981); p. 765 - 770 View in Reaxys Reaction Steps: 2 2: 85 percent / 20 percent aqueous TiCl3 / tetrahydrofuran / 4 h With titanium(III) chloride in tetrahydrofuran

32/122

2016-03-14 02:10:57

Wade, Peter A.; Hinney, Harry R.; Amin, Nayan V.; Vail, Peter D.; Morrow, Scott D.; et al.; Journal of Organic Chemistry; vol. 46; (1981); p. 765 - 770 View in Reaxys

(v2)

Cl Zn

Rx-ID: 3873013 View in Reaxys 61/395 Yield

Conditions & References

68 %

With bis(acetylacetonate)nickel(II), diphenylcyclohexyl phosphine in tetrahydrofuran, Time= 1h, T= 20 °C , Yields of byproduct given Frejd, Torbjoern; Klingstedt, Tomas; Synthesis; nb. 1; (1987); p. 40 - 42 View in Reaxys

N Si O

N O

Rx-ID: 3949102 View in Reaxys 62/395 Yield

Conditions & References

61 %, 23 % With titanium tetrachloride, zinc in tetrahydrofuran, dichloromethane, Time= 3h, T= -15 °C Uno, Hidemitsu; Fujiki, Satomi; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 59; nb. 4; (1986); p. 1267 - 1268 View in Reaxys 23 %, 61 % With titanium tetrachloride, zinc in tetrahydrofuran, dichloromethane, Time= 3h, T= -15 °C Uno, Hidemitsu; Fujiki, Satomi; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 59; nb. 4; (1986); p. 1267 - 1268 View in Reaxys N O

N O

Rx-ID: 4030655 View in Reaxys 63/395 Yield

Conditions & References

55 %, 30 % With titanium tetrachloride, zinc in tetrahydrofuran, dichloromethane, Time= 3h, T= -15 °C Uno, Hidemitsu; Fujiki, Satomi; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 59; nb. 4; (1986); p. 1267 - 1268 View in Reaxys 30 %, 55 % With titanium tetrachloride, zinc in tetrahydrofuran, dichloromethane, Time= 3h, T= -15 °C Uno, Hidemitsu; Fujiki, Satomi; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 59; nb. 4; (1986); p. 1267 - 1268 View in Reaxys

C–

N N+

Rx-ID: 29502575 View in Reaxys 64/395 Yield 95 %

Conditions & References With H3[PW12O40], Time= 0.0333333h, T= 130 - 142 °C , Microwave irradiation, Ionic liquid, chemoselective reaction

33/122

2016-03-14 02:10:57

Mohammadpoor-Baltork, Iraj; Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiolah; Mirjafari, Arsalan; Comptes Rendus Chimie; vol. 13; nb. 12; (2010); p. 1468 - 1473 View in Reaxys 88 %

O Br

O–

+ N Na

Rx-ID: 30891713 View in Reaxys 65/395 Yield

Conditions & References

84 %

Rx-ID: 604999 View in Reaxys 66/395 Yield 93.8 %

Conditions & References With 18-crown-6 ether in acetonitrile, Time= 12h, T= 18 °C Cox, Russell J.; O'Hagan, David; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 10; (1991); p. 2537 - 2540 View in Reaxys Cannizzaro; Justus Liebigs Annalen der Chemie; vol. 96; (1855); p. 246 View in Reaxys Cannizzaro; Justus Liebigs Annalen der Chemie; vol. 96; (1855); p. 246 View in Reaxys

80 % Chro- With aluminum oxide in cyclohexane, Time= 72h, T= 50 °C , Irradiation, ultrasound mat. Ando, Takashi; Kawate, Takehiko; Ichihara, Junko (nee Yamawaki); Hanafusa, Terukiyo; Chemistry Letters; (1984); p. 725 - 728 View in Reaxys With ethanol Lesslie; Turner; Journal of the Chemical Society; (1929); p. 1516 View in Reaxys With S,S-dimethyl-sulfimide in methanol, T= 60 °C , Yield given Furukawa, Naomichi; Takahashi, Fujio; Yoshimura, Toshiaki; Morita, Hiroyuki; Oae, Shigeru; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1981); p. 432 - 437 View in Reaxys With ethanol, water Mann; Chemische Berichte; vol. 14; (1881); p. 1646 View in Reaxys With cross-linked polystyrene resin in water, toluene, T= 90 °C , initial rate of the reaction, other temperature and catalysts, variation of benzyl chloride concentrations, Equilibrium constant

34/122

2016-03-14 02:10:57

Takeuchi, Hirofumi; Kikuchi, Masahiro; Miwa, Yoshihisa; Okada, Yutaro; Chemical & Pharmaceutical Bulletin; vol. 30; nb. 11; (1982); p. 3865 - 3871 View in Reaxys 71 % Chro- With Amberlite XAD-2 resin, water, Time= 24h, T= 65 °C , other alkyl halides and other anions: KOAc or KI; var. mat. macroporous polymer resins, time, and amounts of water, Product distribution Sukata, Kazuaki; Journal of Organic Chemistry; vol. 50; nb. 22; (1985); p. 4388 - 4390 View in Reaxys With aluminum oxide in cyclohexane, Time= 72h, T= 50 °C , Irradiation, various solvents and time, Product distribution Ando, Takashi; Kawate, Takehiko; Ichihara, Junko (nee Yamawaki); Hanafusa, Terukiyo; Chemistry Letters; (1984); p. 725 - 728 View in Reaxys With 2,3,11,12-dicyclohexano-1,4,7,10,13,16-hexaoxacyclo-octadecane, water in chlorobenzene, Time= 24h, T= 100 °C , half-life times Dehmlow, Eckehard V.; Raths, Hans-Christian; Journal of Chemical Research, Miniprint; nb. 12; (1988); p. 2901 2917 View in Reaxys With S,S-dimethyl-sulfimide, T= 60 °C , effect of mixed solvents on the rate, Rate constant Furukawa, Naomichi; Takahashi, Fujio; Yoshimura, Toshiaki; Morita, Hiroyuki; Oae, Shigeru; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1981); p. 432 - 437 View in Reaxys in acetonitrile, Heating, var. support materials; other phenyl chlorides and solvents, Product distribution Clark, James H.; Duke, Catherine V. A.; Journal of Organic Chemistry; vol. 50; nb. 8; (1985); p. 1330 - 1332 View in Reaxys With 1-n-butyl-3-methylimidazolium hexafluorophosphate, T= 80 °C , Kinetics, Further Variations: Temperatures Wheeler; West; Liotta; Eckert; Chemical Communications; nb. 10; (2001); p. 887 - 888 View in Reaxys H N HO N

Rx-ID: 1987933 View in Reaxys 67/395 Yield 94 %

Conditions & References With phosphorus tribromide in benzene, Time= 5h, Heating Liguori, Angelo; Sindona, Giovanni; Romeo, Giovanni; Uccella, Nicola; Synthesis; nb. 2; (1987); p. 168 View in Reaxys

C N O

H N

S O

Rx-ID: 2684539 View in Reaxys 68/395 Yield 67 %

Conditions & References With potassium tert-butylate in ethylene glycol dimethyl ether, Time= 0.5h, T= -55 °C Leusen, Albert M. van; Oomkes, Piet G.; Synthetic Communications; vol. 10; nb. 5; (1980); p. 399 - 404 View in Reaxys

35/122

2016-03-14 02:10:57

Si HO

Rx-ID: 3838807 View in Reaxys 69/395 Yield

Conditions & References

98 %

With chloro-trimethyl-silane, sodium iodide in N,N-dimethyl-formamide, acetonitrile, Time= 2h, T= 60 - 65 °C , Product distribution, Mechanism Davis, Roman; Untch, Karl G.; Journal of Organic Chemistry; vol. 46; nb. 14; (1981); p. 2985 - 2987 View in Reaxys N

O O

N O

Rx-ID: 3949109 View in Reaxys 70/395 Yield

Conditions & References

46 %, 20 % With titanium tetrachloride, zinc in tetrahydrofuran, dichloromethane, Time= 3h, T= -15 °C Uno, Hidemitsu; Fujiki, Satomi; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 59; nb. 4; (1986); p. 1267 - 1268 View in Reaxys 20 %, 46 % With titanium tetrachloride, zinc in tetrahydrofuran, dichloromethane, Time= 3h, T= -15 °C Uno, Hidemitsu; Fujiki, Satomi; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 59; nb. 4; (1986); p. 1267 - 1268 View in Reaxys

O N O

N O

N OH

Rx-ID: 4646724 View in Reaxys 71/395 Yield

Conditions & References

94 %, 100 %

With 2,2'-azo-bisisobutyronitrile, tri-n-butyl-tin hydride in benzene, Heating Chang, Rae Kyu; Kim, Kyongtae; Tetrahedron Letters; vol. 37; nb. 43; (1996); p. 7791 - 7794 View in Reaxys

100 %, 94 %

With 2,2'-azo-bisisobutyronitrile, tri-n-butyl-tin hydride in benzene, Heating Chang, Rae Kyu; Kim, Kyongtae; Tetrahedron Letters; vol. 37; nb. 43; (1996); p. 7791 - 7794 View in Reaxys

O O

N NH 2

Rx-ID: 2091161 View in Reaxys 72/395 Yield 80 %

Conditions & References With iodosylbenzene in dichloromethane, Time= 0.5h, Ambient temperature, molecular sieves (4 A) Mueller, Paul; Gilabert, David Manuel; Tetrahedron; vol. 44; nb. 23; (1988); p. 7171 - 7176 View in Reaxys

36/122

2016-03-14 02:10:57

Rx-ID: 2399756 View in Reaxys 73/395 Yield

Conditions & References

93 %

With N,N,N',N'-tetramethylguanidine in acetonitrile Dowd; Wilk; Wlostowski; Synthetic Communications; vol. 23; nb. 16; (1993); p. 2323 - 2329 View in Reaxys With lithium hydride, 1.) THF, room temperature, 1 h, 2.) THF, room temperature, 2 h, Yield given. Multistep reaction Tsuruoka, Akihiko; Negi, Shigeto; Yanagisawa, Manabu; Nara, Kazumasa; Naito, Toshihiko; Minami, Norio; Synthetic Communications; vol. 27; nb. 20; (1997); p. 3547 - 3557 View in Reaxys

O HO

NH 2

Rx-ID: 4516774 View in Reaxys 74/395 Yield

Conditions & References

77 %

With pyridine, trichloroisocyanuric acid in methanol Hiegel, Gene A.; Lewis, Justin C.; Bae, Jason W.; Synthetic Communications; vol. 34; nb. 19; (2004); p. 3449 - 3453 View in Reaxys

53 %

With copper(ll) bromide, lithium tert-butylate in tetrahydrofuran, hexane, Time= 2.5h, Ambient temperature Takeda, Takeshi; Yamauchi, Satoshi; Fujiwara, Tooru; Synthesis; nb. 5; (1996); p. 600 - 602 View in Reaxys

n-hexyl halide

NH 2

Rx-ID: 12458125 View in Reaxys 75/395 Yield

Conditions & References Reaction Steps: 2 1: 3 g / sodium azide; trifluoromethanesulfonic anhydride; pyridine / copper(II) sulfate / CH2Cl2 / 18 h 2: 36 percent / pyridinium chlorochromate / CH2Cl2 / 0 - 20 °C With pyridine, sodium azide, trifluoromethanesulfonic acid anhydride, pyridinium chlorochromate, copper(II) sulfate in dichloromethane Fan, Qiu-Hua; Ni, Nan-Ting; Li, Qin; Zhang, Li-He; Ye, Xin-Shan; Organic Letters; vol. 8; nb. 5; (2006); p. 1007 1009 View in Reaxys O O

NH 2

n-hexyl halide

Rx-ID: 12458216 View in Reaxys 76/395 Yield

Conditions & References Reaction Steps: 3 1: sodium borohydride / methanol / 20 °C 2: 3 g / sodium azide; trifluoromethanesulfonic anhydride; pyridine / copper(II) sulfate / CH2Cl2 / 18 h 3: 36 percent / pyridinium chlorochromate / CH2Cl2 / 0 - 20 °C With pyridine, sodium tetrahydroborate, sodium azide, trifluoromethanesulfonic acid anhydride, pyridinium chlorochromate, copper(II) sulfate in methanol, dichloromethane

37/122

2016-03-14 02:10:57

Fan, Qiu-Hua; Ni, Nan-Ting; Li, Qin; Zhang, Li-He; Ye, Xin-Shan; Organic Letters; vol. 8; nb. 5; (2006); p. 1007 1009 View in Reaxys

N N

O O

Rx-ID: 25983533 View in Reaxys 77/395 Yield

Conditions & References

58 % Chro- With G6P, HCl buffer, tri-(hydroxymethyl)-methylamine, Leuconostoc mesenteroides glucose-6-phosphate dehydromat., 14 % genase, NADPH in ethyl acetate, Time= 48h, T= 30 °C , pH= 8.0, Baeyer-Villiger oxidation Chromat. Rodriguez, Cristina; de Gonzalo, Gonzalo; Torres Pazmino, Daniel E.; Fraaije, Marco W.; Gotor, Vicente; Tetrahedron Asymmetry; vol. 19; nb. 2; (2008); p. 197 - 203 View in Reaxys 33 %Chro- With glucose-6-phosphate dehydrogenase, Glc 6P, phenylacetone monooxygenase, NADPH, Time= 48h, T= 30 °C , mat., 22 pH= 8, aq. buffer, Ionic liquid, Baeyer-Villiger oxidation, optical yield given as percent ee, enantioselective reaction %Chromat. Rodriguez, Cristina; De Gonzalo, Gonzalo; Fraaije, Marco W.; Gotor, Vicente; Green Chemistry; vol. 12; nb. 12; (2010); p. 2255 - 2260 View in Reaxys

Rx-ID: 25983534 View in Reaxys 78/395 Yield

Conditions & References

11 % Chro- With G6P, HCl buffer, tri-(hydroxymethyl)-methylamine, Leuconostoc mesenteroides glucose-6-phosphate dehydromat. genase, NADPH in ethyl acetate, Time= 48h, T= 30 °C , pH= 8.0, Baeyer-Villiger oxidation Rodriguez, Cristina; de Gonzalo, Gonzalo; Torres Pazmino, Daniel E.; Fraaije, Marco W.; Gotor, Vicente; Tetrahedron Asymmetry; vol. 19; nb. 2; (2008); p. 197 - 203 View in Reaxys 56 %Chromat.

With glucose-6-phosphate dehydrogenase, Glc 6P, phenylacetone monooxygenase, NADPH in dimethyl sulfoxide, Time= 48h, T= 30 °C , pH= 8, aq. buffer, Baeyer-Villiger oxidation, optical yield given as percent ee, enantioselective reaction Rodriguez, Cristina; De Gonzalo, Gonzalo; Fraaije, Marco W.; Gotor, Vicente; Green Chemistry; vol. 12; nb. 12; (2010); p. 2255 - 2260 View in Reaxys

26 %Chromat.

With glucose-6-phosphate dehydrogenase, Glc 6P, phenylacetone monooxygenase, NADPH, Time= 48h, T= 30 °C , pH= 8, aq. buffer, Ionic liquid, Baeyer-Villiger oxidation, optical yield given as percent ee, enantioselective reaction Rodriguez, Cristina; De Gonzalo, Gonzalo; Fraaije, Marco W.; Gotor, Vicente; Green Chemistry; vol. 12; nb. 12; (2010); p. 2255 - 2260 View in Reaxys

C–

Cu +

Rx-ID: 28190114 View in Reaxys 79/395 Yield 87 %

Conditions & References in tetrahydrofuran, Time= 10h, T= 80 °C

38/122

2016-03-14 02:10:57

Bhor, Malhari D.; Panda, Anil G.; Nandurkar, Nitin S.; Bhanage, Bhalchandra M.; Tetrahedron Letters; vol. 49; nb. 45; (2008); p. 6475 - 6479 View in Reaxys

Rx-ID: 35746866 View in Reaxys 80/395 Yield

Conditions & References

51 %

With trimethylsilylazide, silver carbonate in dimethyl sulfoxide, Time= 12h, T= 100 °C Shen, Tao; Wang, Teng; Qin, Chong; Jiao, Ning; Angewandte Chemie - International Edition; vol. 52; nb. 26; (2013); p. 6677 - 6680; Angew. Chem.; vol. 125; nb. 26; (2013); p. 6809 - 6612,4 View in Reaxys H C–

Na +

Rx-ID: 578224 View in Reaxys 81/395 Yield

Conditions & References With diethyl ether, sodium Upson; Maxwell; Parmelee; Journal of the American Chemical Society; vol. 52; (1930); p. 1971,1974 View in Reaxys Rising; Zee; Journal of the American Chemical Society; vol. 50; (1928); p. 1704 View in Reaxys Rising; Braun; Journal of the American Chemical Society; vol. 52; (1930); p. 1070,1072 View in Reaxys With diethyl ether, sodium amide Upson; Thompson; Journal of the American Chemical Society; vol. 44; (1922); p. 182 View in Reaxys Bodroux; Taboury; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 150; (1910); p. 532; Bulletin de la Societe Chimique de France; vol. <4> 7; (1910); p. 667 View in Reaxys

N O

Rx-ID: 2062732 View in Reaxys 82/395 Yield

Conditions & References

70 %

With titanium tetrachloride, tetraethylammonium p-toluenesulfonate in N,N-dimethyl-formamide, electroreduction - 5 mA/cm2 Sera, Akira; Tani, Hiroyuki; Nishiguchi, Ikuzo; Hirashima, Tsuneaki; Synthesis; nb. 7; (1987); p. 631 - 633 View in Reaxys N Si

N O

Rx-ID: 3949103 View in Reaxys 83/395 Yield

Conditions & References

33 %, 21 % With titanium tetrachloride, zinc in tetrahydrofuran, dichloromethane, Time= 3h, T= -15 °C Uno, Hidemitsu; Fujiki, Satomi; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 59; nb. 4; (1986); p. 1267 - 1268

39/122

2016-03-14 02:10:57

View in Reaxys 21 %, 33 % With titanium tetrachloride, zinc in tetrahydrofuran, dichloromethane, Time= 3h, T= -15 °C Uno, Hidemitsu; Fujiki, Satomi; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 59; nb. 4; (1986); p. 1267 - 1268 View in Reaxys

polymer-bound NMe3 (1+)*CN(1-)

Rx-ID: 8989140 View in Reaxys 84/395 Yield

Conditions & References in benzene, Time= 12h, T= 70 °C Kirschning, Andreas; Altwicker, Carsten; Drger, Gerald; Harders, Jan; Hoffmann, Nora; Hoffmann, Ulrich; Schnfeld, Hagen; Solodenko, Wladimir; Kunz, Ulrich; Angewandte Chemie - International Edition; vol. 40; nb. 21; (2001); p. 3995 - 3998 View in Reaxys

13C

N 13C Na

Rx-ID: 9324591 View in Reaxys 85/395 Yield

Conditions & References

74.6 %

Stage 1: in ethanol, water, Time= 6h, Heating Stage 2: With thiourea in ethanol, water, Time= 1h, Heating Corrie, John E. T.; Ranjit; Munasinghe; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 48; nb. 3; (2005); p. 231 - 233 View in Reaxys

69 %

Fathi, Behrouz; Giovannini, Edgardo; Helvetica Chimica Acta; vol. 85; nb. 7; (2002); p. 2083 - 2088 View in Reaxys

2H 2H

Rx-ID: 18733233 View in Reaxys 86/395 Yield

Conditions & References Reaction Steps: 2 1: 75 percent / NBS 2: 61 percent / ethane-1,2-diol / 110 °C With N-bromosuccinmide in ethylene glycol Wierlacher, Stefan; Sander, Wolfram; Uu, Michael T. H.; Journal of the American Chemical Society; vol. 115; nb. 20; (1993); p. 8943 - 8953 View in Reaxys H

14C 2

H 14 2 C

Rx-ID: 2034617 View in Reaxys 87/395 Yield

Conditions & References With tetrabutylammomium bromide in dichloromethane, water, Yield given

40/122

2016-03-14 02:10:57

Miller, David J.; Subramanian, Rm.; Saunders, William H.; Journal of the American Chemical Society; vol. 103; nb. 12; (1981); p. 3519 - 3522 View in Reaxys

N O

O P O

Rx-ID: 2170227 View in Reaxys 88/395 Yield

Conditions & References With samarium diiodide, tert-butyl alcohol in tetrahydrofuran, Time= 2h, Ambient temperature, Yield given Yoneda, Ryuji; Harusawa, Shinya; Kurihara, Takushi; Tetrahedron Letters; vol. 30; nb. 28; (1989); p. 3681 - 3684 View in Reaxys With samarium diiodide, tert-butyl alcohol in tetrahydrofuran, Time= 2h, Ambient temperature, Yield given Yoneda, Ryuji; Harusawa, Shinya; Kurihara, Takushi; Journal of Organic Chemistry; vol. 56; nb. 5; (1991); p. 1827 - 1832 View in Reaxys With hydrogen, palladium on activated charcoal in ethyl acetate, Time= 2h, Ambient temperature, Yield given Hurusawa, Shinya; Nakamura, Shuji; Yagi, Sayoko; Kurihara, Takushi; Hamada, Yasumasa; Shioiri, Takayuki; Synthetic Communications; vol. 14; nb. 14; (1984); p. 1365 - 1372 View in Reaxys

O N NH 2

Rx-ID: 2951113 View in Reaxys 89/395 Yield 88 %

Conditions & References With aluminum oxide, LutClO4 in dichloromethane, constant current electrolysis Ohmori, Hidenobu; Sakai, Kiyoshi; Nagai, Noriko; Mizuki, Yasuyuki; Masui, Masaichiro; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 1; (1985); p. 373 - 376 View in Reaxys

Rx-ID: 3737403 View in Reaxys 90/395 Yield 47 %, 16 %, 31 %

Conditions & References With sodium amide in ethylene glycol dimethyl ether, T= -30 °C Carre, M. C.; Ezzinadi, A. S.; Zouaoui, M. A.; Geoffroy, P.; Caubere, P.; Synthetic Communications; vol. 19; nb. 19; (1989); p. 3323 - 3330 View in Reaxys

47 %, 31 %, 16 %

With sodium amide in ethylene glycol dimethyl ether, T= -30 °C Carre, M. C.; Ezzinadi, A. S.; Zouaoui, M. A.; Geoffroy, P.; Caubere, P.; Synthetic Communications; vol. 19; nb. 19; (1989); p. 3323 - 3330 View in Reaxys

41/122

2016-03-14 02:10:57

Si O

N O

Rx-ID: 3949108 View in Reaxys 91/395 Yield

Conditions & References

19 %, 11 % With titanium tetrachloride, zinc in tetrahydrofuran, dichloromethane, Time= 3h, T= -15 °C Uno, Hidemitsu; Fujiki, Satomi; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 59; nb. 4; (1986); p. 1267 - 1268 View in Reaxys 11 %, 19 % With titanium tetrachloride, zinc in tetrahydrofuran, dichloromethane, Time= 3h, T= -15 °C Uno, Hidemitsu; Fujiki, Satomi; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 59; nb. 4; (1986); p. 1267 - 1268 View in Reaxys

Rx-ID: 4731491 View in Reaxys 92/395 Yield

Conditions & References

8 % Chromat., 67 % Chromat.

With -(1-MeO-4-CH2NMe3Cl-C6H2-(CH2)-2-yl-6)4 in water, Time= 12h, T= 60 °C Shimizu, Shoichi; Kito, Katsuyuki; Sasaki, Yasuyuki; Hirai, Choichiro; Chemical Communications; nb. 17; (1997); p. 1629 - 1630 View in Reaxys

C–

N N+

Rx-ID: 9717889 View in Reaxys 93/395 Yield

Conditions & References

96 %

With triphenylphosphine, 2,3-dicyano-5,6-dichloro-p-benzoquinone in acetonitrile, Time= 4h, Heating Akhlaghinia, Batool; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 9; (2004); p. 1783 - 1786 View in Reaxys

O N

O O

Rx-ID: 21640452 View in Reaxys 94/395 Yield

Conditions & References Reaction Steps: 6 1: 1.) Cs2CO3 / 1.) DMF, 80 deg C, 2.) 80 deg C 2: 92 percent / hydrogen / 10 percent Pd/C / dimethylformamide / 4 h / 25 °C / 2280 Torr 3: 1.) Cs2CO3 / 1.) DMF, 80 deg C, 1 h, 2.) 80 deg C, 6 h 4: 86 percent / hydrogen / 10 percent Pd/C / ethyl acetate / 4 h / 25 °C / 2280 Torr 5: 36 percent / NaH / tetrahydrofuran / 4 h / Heating

42/122

2016-03-14 02:10:57

6: 12 h / Ambient temperature With hydrogen, sodium hydride, caesium carbonate, palladium on activated charcoal in tetrahydrofuran, ethyl acetate, N,N-dimethyl-formamide Weber, Edwin; Koehler, Hans-Juergen; Reuter, Hans; Journal of Organic Chemistry; vol. 56; nb. 3; (1991); p. 1236 - 1242 View in Reaxys

O OH

O O

Rx-ID: 21654884 View in Reaxys 95/395 Yield

Conditions & References Reaction Steps: 4 1: 1.) Cs2CO3 / 1.) DMF, 80 deg C, 1 h, 2.) 80 deg C, 6 h 2: 86 percent / hydrogen / 10 percent Pd/C / ethyl acetate / 4 h / 25 °C / 2280 Torr 3: 36 percent / NaH / tetrahydrofuran / 4 h / Heating 4: 12 h / Ambient temperature With hydrogen, sodium hydride, caesium carbonate, palladium on activated charcoal in tetrahydrofuran, ethyl acetate Weber, Edwin; Koehler, Hans-Juergen; Reuter, Hans; Journal of Organic Chemistry; vol. 56; nb. 3; (1991); p. 1236 - 1242 View in Reaxys

O O

Rx-ID: 21660776 View in Reaxys 96/395 Yield

Conditions & References Reaction Steps: 5 1: 92 percent / hydrogen / 10 percent Pd/C / dimethylformamide / 4 h / 25 °C / 2280 Torr 2: 1.) Cs2CO3 / 1.) DMF, 80 deg C, 1 h, 2.) 80 deg C, 6 h 3: 86 percent / hydrogen / 10 percent Pd/C / ethyl acetate / 4 h / 25 °C / 2280 Torr 4: 36 percent / NaH / tetrahydrofuran / 4 h / Heating 5: 12 h / Ambient temperature With hydrogen, sodium hydride, caesium carbonate, palladium on activated charcoal in tetrahydrofuran, ethyl acetate, N,N-dimethyl-formamide Weber, Edwin; Koehler, Hans-Juergen; Reuter, Hans; Journal of Organic Chemistry; vol. 56; nb. 3; (1991); p. 1236 - 1242 View in Reaxys

43/122

2016-03-14 02:10:57

Rx-ID: 21661335 View in Reaxys 97/395 Yield

Conditions & References Reaction Steps: 3 1: 86 percent / hydrogen / 10 percent Pd/C / ethyl acetate / 4 h / 25 °C / 2280 Torr 2: 36 percent / NaH / tetrahydrofuran / 4 h / Heating 3: 12 h / Ambient temperature With hydrogen, sodium hydride, palladium on activated charcoal in tetrahydrofuran, ethyl acetate Weber, Edwin; Koehler, Hans-Juergen; Reuter, Hans; Journal of Organic Chemistry; vol. 56; nb. 3; (1991); p. 1236 - 1242 View in Reaxys

N O

Rx-ID: 29160173 View in Reaxys 98/395 Yield

Conditions & References

38 %

With cis-[ReO2I(PPh3)2], dimethylphenylsilane in toluene, Time= 36h, Reflux De Noronha, Rita G.; Romao, Carlos C.; Fernandes, Ana C.; Journal of Organic Chemistry; vol. 74; nb. 18; (2009); p. 6960 - 6964 View in Reaxys

C–

N+

Rx-ID: 29502571 View in Reaxys 99/395 Yield

Conditions & References

88 %, 19 % With [bmim][InCl4], Time= 0.075h, T= 135 - 140 °C , Microwave irradiation, Neat (no solvent), chemoselective reaction Mirjafari, Arsalan; Mohammadpoor-Baltork, Iraj; Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Khosropour, Ahmad Reza; Tetrahedron Letters; vol. 51; nb. 25; (2010); p. 3274 - 3276 View in Reaxys O

O N

S N

E N

Rx-ID: 2186301 View in Reaxys 100/395

44/122

2016-03-14 02:10:57

Yield

Conditions & References

66.6 %

T= 690 °C , p= 1.5Torr Abramovitch, Rudolph A.; Hendi, Shivakumar B.; Kress, Albert O.; Journal of the Chemical Society, Chemical Communications; nb. 20; (1981); p. 1087 - 1088 View in Reaxys

H 2N

NH N

N N

Rx-ID: 2606735 View in Reaxys 101/395 Yield

Conditions & References

52 %, 41 %, 82 %

With hydrazine hydrate in ethanol, Time= 6h, Heating Ege, Guenter; Franz, Hermann; Journal of Heterocyclic Chemistry; vol. 19; (1982); p. 1267 - 1273 View in Reaxys

82 %, 41 %, 52 %

With hydrazine hydrate in ethanol, Time= 6h, Heating Ege, Guenter; Franz, Hermann; Journal of Heterocyclic Chemistry; vol. 19; (1982); p. 1267 - 1273 View in Reaxys

N O

Rx-ID: 3949105 View in Reaxys 102/395 Yield

Conditions & References

21 %

With titanium tetrachloride, zinc in tetrahydrofuran, dichloromethane, Time= 3h, T= -15 °C , Yields of byproduct given Uno, Hidemitsu; Fujiki, Satomi; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 59; nb. 4; (1986); p. 1267 - 1268 View in Reaxys

21 %

With titanium tetrachloride, zinc in tetrahydrofuran, dichloromethane, Time= 3h, T= -15 °C , Yield given. Yields of byproduct given Uno, Hidemitsu; Fujiki, Satomi; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 59; nb. 4; (1986); p. 1267 - 1268 View in Reaxys

Si O

Rx-ID: 3949106 View in Reaxys 103/395 Yield 22 %

Conditions & References With titanium tetrachloride, zinc in tetrahydrofuran, dichloromethane, Time= 3h, T= -15 °C , Yields of byproduct given Uno, Hidemitsu; Fujiki, Satomi; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 59; nb. 4; (1986); p. 1267 - 1268 View in Reaxys

45/122

2016-03-14 02:10:57

22 %

E N

Si E

Rx-ID: 3949112 View in Reaxys 104/395 Yield

Conditions & References

19 %

OH NZ N

Rx-ID: 9070173 View in Reaxys 105/395 Yield

Conditions & References

89 %

With phenylacetaldoxime dehydratase(Bacillus OxB-1 expres.E.coli) in water, Time= 8h, T= 30 °C , pH= 8.0 Xie; Kato; Asano; Bioscience, biotechnology, and biochemistry; vol. 65; nb. 12; (2001); p. 2666 - 2672 View in Reaxys With aldoxime dehydratase of Fusarium graminearum MAFF305135, Enzyme kinetics Kato, Yasuo; Asano, Yasuhisa; Bioscience, Biotechnology and Biochemistry; vol. 69; nb. 11; (2005); p. 2254 - 2257 View in Reaxys

Rx-ID: 2695932 View in Reaxys 106/395 Yield

Conditions & References

1.5 % With Amberlyst A27, water in toluene, Time= 85h, T= 100 °C Chromat., 98 % Chro- Arrad, Onn; Sasson, Yoel; Journal of Organic Chemistry; vol. 54; nb. 21; (1989); p. 4993 - 4998 View in Reaxys mat.

N F I

O O

O F

Rx-ID: 3450414 View in Reaxys 107/395

46/122

2016-03-14 02:10:57

Yield 33 %

Conditions & References With sodium hydride in various solvent(s), Time= 18h, T= 120 °C Hammond, Gerald B.; Plevey, Raymond G.; Sampson, Paul; Tatlow, John Colin; Journal of Fluorine Chemistry; vol. 40; (1988); p. 81 - 98 View in Reaxys

Polymer-Supported Cyanide

Rx-ID: 5589583 View in Reaxys 108/395 Yield 87 %

Conditions & References in benzene, Time= 3h, Heating Harrison, Charles R.; Hodge, Philip; Synthesis; nb. 4; (1980); p. 299 - 301 View in Reaxys

N 13C Na

13C

Rx-ID: 9077244 View in Reaxys 109/395 Yield 23 %

Conditions & References With potassium carbonate in N,N-dimethyl-formamide, Time= 1h, T= 120 °C Perosa, Alvise; Selva, Maurizio; Tundo, Pietro; Journal of the Chemical Society, Perkin Transactions 2; nb. 5; (2002); p. 1033 - 1037 View in Reaxys

oxygen

phenylcyanopyruvic acid ethyl ester-phenyl‐ hydrazone of mp: 107-108 degree Rx-ID: 18991226 View in Reaxys 110/395

Yield

Conditions & References Reaction Steps: 4 1: 1.) s-BuLi / 1.) THF, hexane, -20 deg C, 1.5; 2.) HMPA, -78 deg C, 45 min; 3.) 0 deg C, 2-3 h 2: acetic acid / ethanol; H2O / 6 h / 60 °C 3: benzene / 7 h / Heating 4: NaOMe / methanol / 4 h / Heating With sec.-butyllithium, sodium methylate, acetic acid in methanol, ethanol, water, benzene Santiago; Meyers; Tetrahedron Letters; vol. 34; nb. 37; (1993); p. 5839 - 5842 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran / 0.08 h / Ambient temperature 2: H2 / Pd/C / ethyl acetate / 2 h / Ambient temperature With hydrogen, palladium on activated charcoal in tetrahydrofuran, ethyl acetate Hurusawa, Shinya; Nakamura, Shuji; Yagi, Sayoko; Kurihara, Takushi; Hamada, Yasumasa; Shioiri, Takayuki; Synthetic Communications; vol. 14; nb. 14; (1984); p. 1365 - 1372 View in Reaxys

Rx-ID: 21445396 View in Reaxys 111/395

47/122

2016-03-14 02:10:57

Yield

Conditions & References Reaction Steps: 2 1: 68 percent / dimethylsulfoxide / 24 h 2: 74 percent / 20 percent aqoeous TiCl3 / tetrahydrofuran / 4 h With titanium(III) chloride in tetrahydrofuran, dimethyl sulfoxide Wade, Peter A.; Hinney, Harry R.; Amin, Nayan V.; Vail, Peter D.; Morrow, Scott D.; et al.; Journal of Organic Chemistry; vol. 46; (1981); p. 765 - 770 View in Reaxys Reaction Steps: 3 1: 68 percent / dimethylsulfoxide / 24 h 3: 85 percent / 20 percent aqueous TiCl3 / tetrahydrofuran / 4 h With titanium(III) chloride in tetrahydrofuran, dimethyl sulfoxide Wade, Peter A.; Hinney, Harry R.; Amin, Nayan V.; Vail, Peter D.; Morrow, Scott D.; et al.; Journal of Organic Chemistry; vol. 46; (1981); p. 765 - 770 View in Reaxys Reaction Steps: 2 1: water; ethanol 2: H2 / not given With H2 in ethanol, water vol. Co: Org.Verb.1; 1.1.3.1.1.2, page 58 - 65 View in Reaxys

Rx-ID: 21473868 View in Reaxys 112/395 Yield

Conditions & References Reaction Steps: 2 1: 82 percent / SnCl4 / 0.67 h / Ambient temperature 2: Zn dust / acetic acid / 1 h / 100 °C With zinc, tin(IV) chloride in acetic acid Tamura; Shindo; Uenishi; Ishibashi; Tetrahedron Letters; vol. 21; nb. 26; (1980); p. 2547 - 2548 View in Reaxys

N Br

B HO

Rx-ID: 31336701 View in Reaxys 113/395 Yield

Conditions & References

68 %Chromat.

With bis(acetylacetonate)nickel(II), potassium phosphate, triphenylphosphine in toluene, Time= 3h, T= 80 °C , Inert atmosphere Yang, Yingying; Tang, Shan; Liu, Chao; Zhang, Huimin; Sun, Zhexun; Lei, Aiwen; Organic and Biomolecular Chemistry; vol. 9; nb. 15; (2011); p. 5343 - 5345 View in Reaxys

Rx-ID: 2395147 View in Reaxys 114/395 Yield 92 %

Conditions & References in tetrahydrofuran, Time= 2h, Heating

48/122

2016-03-14 02:10:57

Harusawa, Shinya; Yoneda, Ryuji; Omori, Yukie; Kurihara, Takushi; Tetrahedron Letters; vol. 28; nb. 36; (1987); p. 4189 - 4190 View in Reaxys

dinitrile of/the/ higher melting α.α'-diphenyl-succinic acid

Rx-ID: 5589579 View in Reaxys 115/395 Yield

Conditions & References With palladium, T= 230 - 250 °C , p= 100 - 110Torr Knoevenagel; Bergdolt; Chemische Berichte; vol. 36; (1903); p. 2861 View in Reaxys

14C

N 14C Na

Rx-ID: 8691652 View in Reaxys 116/395 Yield

Conditions & References

54 %

With tetrabutylammomium bromide in ethanol, water, Time= 6.5h, Heating Shackleford, David M.; Hayball, Peter J.; Reynolds, Geoffrey D.; Hamon, David P. G.; Evans, Allan M.; Milne, Robert W.; Nation, Roger L.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 44; nb. 3; (2001); p. 225 - 234 View in Reaxys

H N

Rx-ID: 21469474 View in Reaxys 117/395 Yield

Conditions & References Reaction Steps: 2 1: lithium cyanide / tetrahydrofuran / 0.5 h / Ambient temperature 2: samarium diiodide, terc-butyl alcohol / tetrahydrofuran / 2 h / Ambient temperature With samarium diiodide, lithium cyanide, tert-butyl alcohol in tetrahydrofuran Yoneda, Ryuji; Harusawa, Shinya; Kurihara, Takushi; Tetrahedron Letters; vol. 30; nb. 28; (1989); p. 3681 - 3684 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran / Ambient temperature 2: SmI2, t-BuOH / tetrahydrofuran / 2 h / Ambient temperature With samarium diiodide, tert-butyl alcohol in tetrahydrofuran Yoneda, Ryuji; Harusawa, Shinya; Kurihara, Takushi; Journal of Organic Chemistry; vol. 56; nb. 5; (1991); p. 1827 - 1832 View in Reaxys

3 Na + N N (v6)

N N

Co 3-

N N

Rx-ID: 26735047 View in Reaxys 118/395

49/122

2016-03-14 02:10:57

Yield

Conditions & References With hydrogen in not given, byproducts: α-methyl-styrol, cumol; on absorption of H2 by alkaline soln., formation of phenyl acetonitrile, α-methylstyrol and cumol; Kwiatek, J.; Seyler, J. K.; Journal of Organometallic Chemistry; vol. 3; (1965); p. 433 - 437 ; (from Gmelin) View in Reaxys With alkali hydroxide in not given, on decompn. with acids and treatment of product with alkali hydroxide; Kwiatek, J.; Seyler, J. K.; Journal of Organometallic Chemistry; vol. 3; (1965); p. 433 - 437 ; (from Gmelin) View in Reaxys With acid, alkali hydroxide in not given, on decompn. with acids and treatment of product with alkali hydroxide; vol. Co: Org.Verb.1; 1.1.3.1.1.2, page 58 - 65 ; (from Gmelin) View in Reaxys With H2 in not given, byproducts: α-methyl-styrol, cumol; on absorption of H2 by alkaline soln., formation of phenyl acetonitrile, α-methylstyrol and cumol; vol. Co: Org.Verb.1; 1.1.3.1.1.2, page 58 - 65 ; (from Gmelin) View in Reaxys

O S NH O

N H

Rx-ID: 37826218 View in Reaxys 119/395 Yield

Conditions & References With caesium carbonate in acetonitrile, T= 20 °C Tang, Hai-Tao; Zhou, Yun-Bing; Zhu, Yu; Sun, Hong-Chao; Lin, Min; Zhan, Zhuang-Ping; Chemistry - An Asian Journal; vol. 9; nb. 5; (2014); p. 1278 - 1281 View in Reaxys H C– K+

Rx-ID: 578220 View in Reaxys 120/395 Yield

Conditions & References With diethyl ether, potassium Rising; Muskat; Lowe; Journal of the American Chemical Society; vol. 51; (1929); p. 263 View in Reaxys N N

Rx-ID: 2167325 View in Reaxys 121/395 Yield 71 %

Conditions & References With nickel Reetz, M. T.; Mueller-Starke, H.; Tetrahedron Letters; vol. 25; nb. 31; (1984); p. 3301 - 3304 View in Reaxys

50/122

2016-03-14 02:10:57

Rx-ID: 2184575 View in Reaxys 122/395 Yield

Conditions & References

86 %

in toluene, Time= 1h, Heating Tamura, Yasumitsu; Adachi, Masahiro; Kawasaki, Tomomi; Yasuda, Hitoshi; Kita, Yasuyuki; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1132 - 1135 View in Reaxys

N+

S N

I–

Rx-ID: 2256984 View in Reaxys 123/395 Yield

Conditions & References

80 %

in ethylene glycol dimethyl ether, Time= 24h, Heating Fresneda, P. M.; Lidon, M. J.; Molina, P.; Vilaplana, M. J.; Synthesis; nb. 9; (1981); p. 711 - 714 View in Reaxys

P O

Rx-ID: 9803335 View in Reaxys 124/395 Yield 20 % Spectr.

Conditions & References With 2,6-dimethyl-1,4-benzoquinone in dichloromethane, Time= 24h, T= 20 °C Mukaiyama, Teruaki; Masutani, Kouta; Hagiwara, Yoshiaki; Chemistry Letters; vol. 33; nb. 9; (2004); p. 1192 - 1193 View in Reaxys

Rx-ID: 21472211 View in Reaxys 125/395 Yield

Conditions & References Reaction Steps: 2 1: 73 percent / dimethylsulfoxide / 24 h 2: 74 percent / 20 percent aqoeous TiCl3 / tetrahydrofuran / 4 h With titanium(III) chloride in tetrahydrofuran, dimethyl sulfoxide Wade, Peter A.; Hinney, Harry R.; Amin, Nayan V.; Vail, Peter D.; Morrow, Scott D.; et al.; Journal of Organic Chemistry; vol. 46; (1981); p. 765 - 770 View in Reaxys Reaction Steps: 3 1: 73 percent / dimethylsulfoxide / 24 h

51/122

2016-03-14 02:10:57

3: 85 percent / 20 percent aqueous TiCl3 / tetrahydrofuran / 4 h With titanium(III) chloride in tetrahydrofuran, dimethyl sulfoxide Wade, Peter A.; Hinney, Harry R.; Amin, Nayan V.; Vail, Peter D.; Morrow, Scott D.; et al.; Journal of Organic Chemistry; vol. 46; (1981); p. 765 - 770 View in Reaxys

O O

Cl O

Rx-ID: 25278733 View in Reaxys 126/395 Yield

Conditions & References 9 : EXAMPLE 9 EXAMPLE 9 A solution of 2.44 g. (0.01 m.) of 3-carbomethoxy-4-methoxyphenethylamine (prepared from 3-carbomethoxy-4-methoxybenzyl chloride by reaction with sodium cyanide followed by catalytic reduction of the resulting benzyl nitrile) in 25 ml. of toluene is refluxed azeotropically with 1.27 g. (0.012 m.) of benzaldehyde for one hour, then the solution is concentrated to give the N-benzal derivative. Patent; SmithKline Corporation; US3933913; (1976); (A1) English View in Reaxys

N N

Rx-ID: 25983532 View in Reaxys 127/395 Yield

Conditions & References With sodium hydroxide in ethyl acetate, T= 20 °C Rodriguez, Cristina; de Gonzalo, Gonzalo; Torres Pazmino, Daniel E.; Fraaije, Marco W.; Gotor, Vicente; Tetrahedron Asymmetry; vol. 19; nb. 2; (2008); p. 197 - 203 View in Reaxys

Rx-ID: 2083871 View in Reaxys 128/395 Yield 99 %

Conditions & References T= 520 - 550 °C , p= 0.01Torr Meier, Michael; Ruechardt, Christoph; Chemische Berichte; vol. 120; (1987); p. 1 - 4 View in Reaxys

100 % Chromat.

With 1,1-di(phenyl)ethylene in various solvent(s), T= 210 °C , ΔG(excit.) <250 deg C>; ΔH(excit.), ΔS(excit.), Rate constant, Thermodynamic data Meier, Michael; Mueller, Barbara; Ruechardt, Christoph; Journal of Organic Chemistry; vol. 52; nb. 4; (1987); p. 648 - 652 View in Reaxys With 1,1-diphenylene, chlorobenzene in benzene, T= 170 °C , also at 190, 210 and 230 deg C; ΔHY (excit.), ΔΔHYH(excit.),

ΔSY(excit.), ΔΔSY-H(excit); other solvents, Rate constant, Thermodynamic data

Kim, Sung Soo; Choi, Won Jung; Zhu, Yu; Kim, Jin Hyun; Journal of Organic Chemistry; vol. 63; nb. 4; (1998); p. 1185 - 1189 View in Reaxys

52/122

2016-03-14 02:10:57

N 2

Rx-ID: 21517930 View in Reaxys 129/395 Yield

Conditions & References Reaction Steps: 2 1: NBS 2: aq. ethanol With N-bromosuccinmide in ethanol Chao, Herbert S.-I.; Berchtold, Glenn A.; Journal of Organic Chemistry; vol. 46; nb. 6; (1981); p. 1191 - 1194 View in Reaxys

N Cl

Cl O

Rx-ID: 21631361 View in Reaxys 130/395 Yield

Conditions & References Reaction Steps: 2 1: 36 percent / NaH / tetrahydrofuran / 4 h / Heating 2: 12 h / Ambient temperature With sodium hydride in tetrahydrofuran Weber, Edwin; Koehler, Hans-Juergen; Reuter, Hans; Journal of Organic Chemistry; vol. 56; nb. 3; (1991); p. 1236 - 1242 View in Reaxys

O O

Rx-ID: 21658864 View in Reaxys 131/395 Yield

53/122

2016-03-14 02:10:57

O–

3 S

Ga 3+ N

H O

H 3

H N+ HH

H O–

O 3

2 O–

O N

C+

Ga 3+ S

N+ HH

Rx-ID: 27442006 View in Reaxys 132/395 Yield

Conditions & References With 18-crown-6 in water, Electrochem. Process; crysts. grew on the anode for 8-10 d in C6H5CH2CN/H2O Akutsu, Hiroki; Akutsu-Sato, Akane; Turner, Scott S.; Day, Peter; Canadell, Enric; Firth, Steven; Clark, Robin J. H.; Yamada, Jun-Ichi; Nakatsuji, Shin'ichi; Chemical Communications; nb. 1; (2004); p. 18 - 19 ; (from Gmelin) View in Reaxys 2H

2H 2H

Br 2H

Rx-ID: 27967160 View in Reaxys 133/395 Yield

Conditions & References

10.1 g

With tetrabutylammomium bromide in water, Time= 8h, T= 120 °C Zhao, Hong; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 7; (2008); p. 293 - 296 View in Reaxys

S+

Br–

O S

N NH 2

Rx-ID: 28943146 View in Reaxys 134/395 Yield

Conditions & References

78 %

in acetonitrile, Time= 3.5h, Reflux Yadav, Lal Dhar S.; Srivastava, Vishnu P.; Patel, Rajesh; Tetrahedron Letters; vol. 50; nb. 39; (2009); p. 5532 5535 View in Reaxys

N NH 2

Rx-ID: 30029085 View in Reaxys 135/395 Yield

Conditions & References With NiII chloride hexahydrate, Time= 18h, T= 155 °C , Inert atmosphere Allen, C. Liana; Davulcu, Simge; Williams, Jonathan M. J.; Organic Letters; vol. 12; nb. 22; (2010); p. 5096 - 5099 View in Reaxys

N O O–

K+

Rx-ID: 30891809 View in Reaxys 136/395

54/122

2016-03-14 02:10:57

Yield

Conditions & References

10 %Chro- With tris-(dibenzylideneacetone)dipalladium(0), 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl in 1,3,5-trimat., 28 methyl-benzene, Time= 5.16667h, T= 20 - 140 °C , Inert atmosphere, Sealed tube %Chromat. Shang, Rui; Ji, Dong-Sheng; Chu, Ling; Fu, Yao; Liu, Lei; Angewandte Chemie - International Edition; vol. 50; nb. 19; (2011); p. 4470 - 4474 View in Reaxys 69 %Chro- With dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine, tris-(dibenzylideneacetone)dipalladium(0) in 1,3,5-trimethylmat., 10 benzene, Time= 5.16667h, T= 20 - 140 °C , Inert atmosphere, Sealed tube %Chromat. Shang, Rui; Ji, Dong-Sheng; Chu, Ling; Fu, Yao; Liu, Lei; Angewandte Chemie - International Edition; vol. 50; nb. 19; (2011); p. 4470 - 4474 View in Reaxys

O + N Na

O–

Rx-ID: 30891820 View in Reaxys 137/395 Yield

Conditions & References

9 %ChroWith dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine, tris-(dibenzylideneacetone)dipalladium(0) in N,N-dimethyl mat., 23 acetamide, Time= 5.16667h, T= 20 - 140 °C , Inert atmosphere, Sealed tube %Chromat. Shang, Rui; Ji, Dong-Sheng; Chu, Ling; Fu, Yao; Liu, Lei; Angewandte Chemie - International Edition; vol. 50; nb. 19; (2011); p. 4470 - 4474 View in Reaxys 80 %Chro- With dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine, tris-(dibenzylideneacetone)dipalladium(0) in diethylene glymat., 6 col dimethyl ether, Time= 5.16667h, T= 20 - 140 °C , Inert atmosphere, Sealed tube %Chromat. Shang, Rui; Ji, Dong-Sheng; Chu, Ling; Fu, Yao; Liu, Lei; Angewandte Chemie - International Edition; vol. 50; nb. 19; (2011); p. 4470 - 4474 View in Reaxys

H H 2N

Rx-ID: 33763123 View in Reaxys 138/395 Yield

Conditions & References With dihydrogen peroxide, sodium bromide in water, Time= 5h, T= 20 °C , pH= 5.6, aq. buffer, Enzymatic reaction But, Andrada; Le Notre, Jerome; Scott, Elinor L.; Wever, Ron; Sanders, Johan P. M.; ChemSusChem; vol. 5; nb. 7; (2012); p. 1199 - 1202 View in Reaxys

N 2H

HO 2H

2H 2H

Rx-ID: 39808863 View in Reaxys 139/395 Yield 460 mg

Conditions & References With potassium phosphate, Ni(acac)2, triphenylphosphine in toluene, Time= 3h, T= 80 °C , Inert atmosphere Takamatsu, Kazutaka; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3242 - 3249 View in Reaxys

55/122

2016-03-14 02:10:57

Rx-ID: 40157072 View in Reaxys 140/395 Yield

Conditions & References Stage 1: With n-butyllithium in tetrahydrofuran, Time= 1h, T= -78 °C , Inert atmosphere Stage 2: in tetrahydrofuran, Inert atmosphere Zhu, Xiaolei; Zhang, Mengmeng; Liu, Jingjing; Ge, Jingming; Yang, Guangfu; Journal of Agricultural and Food Chemistry; vol. 63; nb. 13; (2015); p. 3377 - 3386 View in Reaxys

H 2N

O N

Rx-ID: 1837488 View in Reaxys 141/395 Yield

Conditions & References in gas, T= 750 °C , p= 0.001Torr , flash vacuum pyrolysis, Product distribution Wentrup,C.; Briehl,H.; Lorencak,P.; Journal of the American Chemical Society; vol. 110; (1988); p. 1337 View in Reaxys H

13C 2

H 13 2 C

Rx-ID: 2034613 View in Reaxys 142/395 Yield

Conditions & References

83 %

With 18-crown-6 ether, carbon tetrabromide, triphenylphosphine, Time= 25h, Ambient temperature, 1.) MeCN, 2.) MeCN Franke, Wilfried; Frenking, Gernot; Schwarz, Helmut; Wolfschuetz, Roland; Chemische Berichte; vol. 114; (1981); p. 3878 - 3895 View in Reaxys

N 13C

13C

Rx-ID: 2395149 View in Reaxys 143/395 Yield

Conditions & References in dimethyl sulfoxide Baldwin, Michael A.; Gilmore, Jeremy; Mruzek, Margaret N.; Organic Mass Spectrometry; vol. 18; nb. 3; (1983); p. 127 - 129 View in Reaxys in water, dimethyl sulfoxide, Time= 4h, T= 60 °C Holmes, Darren L.; Lightner, David A.; Tetrahedron; vol. 51; nb. 6; (1995); p. 1607 - 1622 View in Reaxys

56/122

2016-03-14 02:10:57

Cl O

Rx-ID: 2643883 View in Reaxys 144/395 Yield

Conditions & References

81.3 %

in dimethyl sulfoxide, Time= 6h Julia, Louis; Suschitzky, H.; Barnes, John C.; Tomlin, Clive D.S.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 10; (1983); p. 2507 - 2511 View in Reaxys

C–

N+

Rx-ID: 2695374 View in Reaxys 145/395 Yield

Conditions & References in water, N,N-dimethyl-formamide, T= 30 °C , also with KCN; var. educts and solvents ratio, Rate constant Jobe, David J.; Westaway, Kenneth Charles; Canadian Journal of Chemistry; vol. 71; nb. 9; (1993); p. 1353 - 1361 View in Reaxys in water, dimethyl sulfoxide, T= 30 °C , other solvent, temperature; 35C/37Cl leaving group, 11C/14C incoming group, 12C/14C carbon kinetic isotope effects for the SN2 reactions between p-substituted benzyl chlorides and cyanide ion, Rate constant Westaway, Kenneth Charles; Van Pham, Thuy; Fang, Yao-Ren; Journal of the American Chemical Society; vol. 119; nb. 16; (1997); p. 3670 - 3676 View in Reaxys in acetonitrile, T= 20 °C Lisowski, Vincent; Enguehard, Cecile; Lancelot, Jean-Charles; Caignard, Daniel-Henri; Lambel, Stephanie; Leonce, Stephane; Pierre, Alain; Atassi, Ghanem; Renard, Pierre; Rault, Sylvain; Bioorganic and Medicinal Chemistry Letters; vol. 11; nb. 16; (2001); p. 2205 - 2208 View in Reaxys

S N NH 2

Rx-ID: 2697526 View in Reaxys 146/395 Yield

Conditions & References

86 %, 90 % With sodium hydroxide, tetrabutylammomium bromide in water, benzene, Time= 2h, T= 30 °C , Product distribution Funakoshi, Yoshio; Takido, Toshio; Itabashi, Kunio; Synthetic Communications; vol. 15; nb. 14; (1985); p. 1299 1304 View in Reaxys 2H

C–

2 Li+

Li+

–

N –

Rx-ID: 9312423 View in Reaxys 147/395 Yield

Conditions & References With n-butyllithium in tetrahydrofuran, hexane

57/122

2016-03-14 02:10:57

Corset, Jacques; Castella-Ventura, Martine; Froment, Francoise; Strzalko, Tekla; Wartski, Lya; Journal of Organic Chemistry; vol. 68; nb. 10; (2003); p. 3902 - 3911 View in Reaxys H C–

2 Li+

Li+

–C –N

Rx-ID: 9321697 View in Reaxys 148/395 Yield

Conditions & References With lithium diisopropyl amide in tetrahydrofuran, Title compound not separated from byproducts Corset, Jacques; Castella-Ventura, Martine; Froment, Francoise; Strzalko, Tekla; Wartski, Lya; Journal of Organic Chemistry; vol. 68; nb. 10; (2003); p. 3902 - 3911 View in Reaxys

N O Br

O–

K+

Rx-ID: 30891712 View in Reaxys 149/395 Yield

Conditions & References

78 %Chro- With tris-(dibenzylideneacetone)dipalladium(0), 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene in 1,3,5-trimethylmat., 7 benzene, Time= 5.16667h, T= 20 - 140 °C , Inert atmosphere, Sealed tube %Chromat. Shang, Rui; Ji, Dong-Sheng; Chu, Ling; Fu, Yao; Liu, Lei; Angewandte Chemie - International Edition; vol. 50; nb. 19; (2011); p. 4470 - 4474 View in Reaxys

Rx-ID: 38681930 View in Reaxys 150/395 Yield

Conditions & References Reaction Steps: 2 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1.5 h / 20 °C 2: dimethyl sulfoxide / 1 h / 100 °C With 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran, dimethyl sulfoxide Lakshman, Mahesh K.; Singh, Manish K.; Kumar, Mukesh; Chamala, Raghu Ram; Yedulla, Vijayender R.; Wagner, Domenick; Leung, Evan; Yang, Lijia; Matin, Asha; Ahmad, Sadia; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 1919 - 1932 View in Reaxys Reaction Steps: 2 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 48 h / 20 °C 2: dimethyl sulfoxide / 1 h / 100 °C With 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran, dimethyl sulfoxide Lakshman, Mahesh K.; Singh, Manish K.; Kumar, Mukesh; Chamala, Raghu Ram; Yedulla, Vijayender R.; Wagner, Domenick; Leung, Evan; Yang, Lijia; Matin, Asha; Ahmad, Sadia; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 1919 - 1932 View in Reaxys

N H 18O

Rx-ID: 38681966 View in Reaxys 151/395

58/122

2016-03-14 02:10:57

Yield

N N S

Z Cl

S S

Rx-ID: 2102972 View in Reaxys 152/395 Yield

Conditions & References

19 %, 34 % With thiozone in N,N-dimethyl-formamide, Time= 7h, Heating Guillanton, Georges le; Do, Quang Tho; Simonet, Jacques; Bulletin de la Societe Chimique de France; nb. 3; (1989); p. 433 - 440 View in Reaxys O HO

N OH

Rx-ID: 2155304 View in Reaxys 153/395 Yield

Conditions & References

85 %

With oxalic acid diimidazolide in benzene, 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h Kitagawa; Kawaguchi; Ikiuchi; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 1; (1991); p. 187 - 189 View in Reaxys

85 %

N– 2

N N

N–

N N

Li+

H C– N

Li+

Rx-ID: 2409279 View in Reaxys 154/395 Yield 31 %

Conditions & References in diethyl ether, hexane, Time= 8h, T= 20 °C

59/122

2016-03-14 02:10:57

Zarges, Wolfgang; Marsch, Michael; Harms, Klaus; Boche, Gernot; Angewandte Chemie; vol. 101; nb. 10; (1989); p. 1424 - 1425 View in Reaxys

H N Si

Rx-ID: 2483386 View in Reaxys 155/395 Yield

Conditions & References

79 %

With phosphorus trichoride in dichloromethane, Ambient temperature Bartoli, Giuseppa; Bosco, Marcella; Dalpozzo, Renato; Marcantoni, Enrico; Tetrahedron Letters; vol. 31; nb. 47; (1990); p. 6935 - 6936 View in Reaxys

79 %

With phosphorus trichoride in dichloromethane, Ambient temperature, other acylsilane phenylhydrazones, Mechanism Bartoli, Giuseppa; Bosco, Marcella; Dalpozzo, Renato; Marcantoni, Enrico; Tetrahedron Letters; vol. 31; nb. 47; (1990); p. 6935 - 6936 View in Reaxys

O HO

Z N HO

Rx-ID: 3068755 View in Reaxys 156/395 Yield

Conditions & References

91 %

With 1,1'-carbonyldiimidazole in benzene, 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h Kitagawa; Kawaguchi; Inoue; Katayama; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 11; (1991); p. 3030 3033 View in Reaxys

91 %

With 1,1'-carbonyldiimidazole in benzene, 1.) r.t., 15 min, 2.) 69-70 deg C, 1 h; other 3-aryl-2-hydroxyiminopropionic acids Kitagawa; Kawaguchi; Inoue; Katayama; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 11; (1991); p. 3030 3033 View in Reaxys

NH N N

Rx-ID: 3257969 View in Reaxys 157/395 Yield

Conditions & References

22 % Time= 9h, T= 450 °C , p= 0.3Torr Spectr., 9 % Spectr., Hoffmann, Reinhard W.; Barth, Wolfgang; Chemische Berichte; vol. 118; nb. 2; (1985); p. 634 - 642 View in Reaxys 49 % Spectr., 41 %

60/122

2016-03-14 02:10:57

N+

NE I–

Rx-ID: 3515013 View in Reaxys 158/395 Yield

Conditions & References With sodium methylate in methanol, Time= 4h, Heating, Yield given Santiago; Meyers; Tetrahedron Letters; vol. 34; nb. 37; (1993); p. 5839 - 5842 View in Reaxys

O O

O– S S

Rx-ID: 3621312 View in Reaxys 159/395 Yield

Conditions & References

51.6 %, 6.9 With Lepidium sativum seeds in neat (no solvent), Time= 1h, T= 125 °C , various temperatures, various times, Product %, 41.5 % distribution Hasapis, Xenophon; MacLeod, Alexander J.; Phytochemistry (Elsevier); vol. 21; nb. 5; (1982); p. 1009 - 1014 View in Reaxys

F F

Rx-ID: 4185598 View in Reaxys 160/395 Yield

Conditions & References With potassium tert-butylate in tetrahydrofuran, Time= 0.25h, Ambient temperature, Yield given Kende, Andrew S.; Tetrahedron Letters; vol. 36; nb. 23; (1995); p. 4035 - 4038 View in Reaxys

Rx-ID: 4838926 View in Reaxys 161/395 Yield

Conditions & References With borate(1-), tetrafluoro-,hydrogen (1:1) ethane, 1,1'-oxybis-, 2-fluoro-pyridine in tetrahydrofuran, di-isopropyl ether, Time= 0.516667h, T= 97 °C , other azadiyne, Product distribution, Mechanism Hoffner, Johannes; Schottelius, Marc J.; Feichtinger, Derek; Chen, Peter; Journal of the American Chemical Society; vol. 120; nb. 2; (1998); p. 376 - 385 View in Reaxys

H 2N

4-[Ph2(AcO)2Bi]-C6H4-OCH2-polystyrene cross-linked with divinylbenzene

C2H5-X Rx-ID: 13346037 View in Reaxys 162/395

61/122

2016-03-14 02:10:57

Yield

Conditions & References Reaction Steps: 2 1: 95 percent / trichloroisocyanuric acid / CH2Cl2 / 1 h / 15 - 20 °C 2: 90 percent / TEA / CH2Cl2 / 2 h / 25 °C With TEA, trichloroisocyanuric acid in dichloromethane De Luca, Lidia; Giacomelli, Giampaolo; Synlett; nb. 12; (2004); p. 2180 - 2184 View in Reaxys

polymer-supported N-benzyloxy-2-nitrobenzenesulfona‐ mide

C2H5-X

Rx-ID: 13352820 View in Reaxys 163/395 Yield

Conditions & References Reaction Steps: 2 1: nBuLi / tetrahydrofuran / 1 h / 0 °C 2: 82 percent Spectr. / 2,6-dimethyl-1,4-benzoquinone / CHCl3 / 24 h / 20 °C With n-butyllithium, 2,6-dimethyl-1,4-benzoquinone in tetrahydrofuran, chloroform Mukaiyama, Teruaki; Masutani, Kouta; Hagiwara, Yoshiaki; Chemistry Letters; vol. 33; nb. 9; (2004); p. 1192 - 1193 View in Reaxys Reaction Steps: 2 1: nBuLi / tetrahydrofuran / 1 h / 0 °C 2: 20 percent Spectr. / 2,6-dimethyl-1,4-benzoquinone / CH2Cl2 / 24 h / 20 °C With n-butyllithium, 2,6-dimethyl-1,4-benzoquinone in tetrahydrofuran, dichloromethane Mukaiyama, Teruaki; Masutani, Kouta; Hagiwara, Yoshiaki; Chemistry Letters; vol. 33; nb. 9; (2004); p. 1192 - 1193 View in Reaxys

2.2-dimethyl-5t(?)-p-tolyl-penten-(4)-one-(3)

Rx-ID: 17461049 View in Reaxys 164/395 Yield

Conditions & References Reaction Steps: 3 1: 84 percent / NaNO2, NaOH / methanol / 0 °C 2: 59 percent / Et3N / CH2Cl2 / Ambient temperature 3: 100 percent / Bu3SnH, AIBN / benzene / Heating With sodium hydroxide, 2,2'-azo-bisisobutyronitrile, tri-n-butyl-tin hydride, triethylamine, sodium nitrite in methanol, dichloromethane, benzene Chang, Rae Kyu; Kim, Kyongtae; Tetrahedron Letters; vol. 37; nb. 43; (1996); p. 7791 - 7794 View in Reaxys

O N O

2.2-dimethyl-5t(?)-p-tolyl-penten-(4)-one-(3)

Rx-ID: 17475782 View in Reaxys 165/395 Yield

Conditions & References Reaction Steps: 2 1: 59 percent / Et3N / CH2Cl2 / Ambient temperature 2: 100 percent / Bu3SnH, AIBN / benzene / Heating With 2,2'-azo-bisisobutyronitrile, tri-n-butyl-tin hydride, triethylamine in dichloromethane, benzene Chang, Rae Kyu; Kim, Kyongtae; Tetrahedron Letters; vol. 37; nb. 43; (1996); p. 7791 - 7794 View in Reaxys

62/122

2016-03-14 02:10:57

2.2-dimethyl-5t(?)-p-tolyl-penten-(4)-one-(3)

Rx-ID: 17631800 View in Reaxys 166/395 Yield

Conditions & References Reaction Steps: 2 1: POCl3, pyridine / benzene 2: 96 percent / NaTeH, AcOH / ethanol; benzene / 0.33 h / -20 °C With pyridine, sodium hydrogen telluride, acetic acid, trichlorophosphate in ethanol, benzene Blay, Gonzalo; Cardona, Luz; Garcia, Begona; Lahoz, Luisa; Pedro, Jose R.; Tetrahedron; vol. 52; nb. 25; (1996); p. 8611 - 8618 View in Reaxys

phenylcyanopyruvic acid ethyl ester-phenyl‐ hydrazone of mp: 107-108 degree

Rx-ID: 18984572 View in Reaxys 167/395 Yield

Conditions & References Reaction Steps: 2 1: benzene / 7 h / Heating 2: NaOMe / methanol / 4 h / Heating With sodium methylate in methanol, benzene Santiago; Meyers; Tetrahedron Letters; vol. 34; nb. 37; (1993); p. 5839 - 5842 View in Reaxys

phenylcyanopyruvic acid ethyl ester-phenyl‐ hydrazone of mp: 107-108 degree

Rx-ID: 18996702 View in Reaxys 168/395 Yield

Conditions & References Reaction Steps: 3 1: acetic acid / ethanol; H2O / 6 h / 60 °C 2: benzene / 7 h / Heating 3: NaOMe / methanol / 4 h / Heating With sodium methylate, acetic acid in methanol, ethanol, water, benzene Santiago; Meyers; Tetrahedron Letters; vol. 34; nb. 37; (1993); p. 5839 - 5842 View in Reaxys

O O

butylamine salts

disulfur dichloride

Rx-ID: 20403220 View in Reaxys 169/395 Yield

Conditions & References Reaction Steps: 2 1: 98 percent / HONH2*HCl, KOH / methanol / 36 h / Ambient temperature 2: 94 percent / PBr3 / benzene / 5 h / Heating With potassium hydroxide, hydroxylamine hydrochloride, phosphorus tribromide in methanol, benzene Liguori, Angelo; Sindona, Giovanni; Romeo, Giovanni; Uccella, Nicola; Synthesis; nb. 2; (1987); p. 168 View in Reaxys

63/122

2016-03-14 02:10:57

S N

Rx-ID: 21441465 View in Reaxys 170/395 Yield

Conditions & References Reaction Steps: 2 1: 84 percent / SnCl4 / CH2Cl2 / 4 h / 0 °C 2: 71 percent / Raney-Ni With tin(IV) chloride, nickel in dichloromethane Reetz, M. T.; Mueller-Starke, H.; Tetrahedron Letters; vol. 25; nb. 31; (1984); p. 3301 - 3304 View in Reaxys

Si O

Rx-ID: 21678569 View in Reaxys 171/395 Yield

Conditions & References Reaction Steps: 2 1: benzene / 1 h / Heating 2: 79 percent / PCl3 / CH2Cl2 / Ambient temperature; other acylsilane phenylhydrazones With phosphorus trichoride in dichloromethane, benzene Bartoli, Giuseppa; Bosco, Marcella; Dalpozzo, Renato; Marcantoni, Enrico; Tetrahedron Letters; vol. 31; nb. 47; (1990); p. 6935 - 6936 View in Reaxys O N N

(v3)

O Ni 2+ 2

C– (v4)

Rx-ID: 26686429 View in Reaxys 172/395 Yield

Conditions & References

80.6 %

in N,N-dimethyl-formamide, Electrolysis; electrolysis of nitrile in soln. of Et4NBr in DMF with Ni anode and Fe cathode (cathodic potential -2.3-2.5V) (N2); addn. of ether, pptn., filtration, washing (MeCN/ether), drying at 70°C (vacuum); elem. anal. Bukhtiarov, A. V.; Kudryavtsev, Yu. G.; Lebedev, A. V.; Golyshin, V. N.; Mikheev, V. V.; Rodnikov, I. A.; Journal of General Chemistry USSR (English Translation); vol. 60; (1990); p. 1189 - 1192; Zhurnal Obshchei Khimii; vol. 60; (1990); p. 1329 - 1332 ; (from Gmelin) View in Reaxys

S F

O–

F 2 F O

Cl –

Fe 2+

N N

N+

N N

64/122

2016-03-14 02:10:57

F F O 2 F S –O O

(v4)

(v4) N

(v4) N (v4) N –Cl Fe 2+ (v4) OC-6 (v4)

(v1)

(v6)

N – (v1) (v4) Cl Fe 2+ (v4) N OC-6 (v6) N (v4)

N N

(v4)

Rx-ID: 27484556 View in Reaxys 173/395 Yield

Conditions & References

15 %

With ascorbic acid in neat (no solvent), byproducts: Bu4NCF3SO3; High Pressure; ligand in benzyl cyanide mixed under stirring with Fe salt in benzyl cyanide followed with ascorbic acid, treated with Bu4NCl in benzyl cyanide,stirred for several min, filtered, heated in a closed tube at 100.degre e.C for 2 d; crystals collected, washed (methanol, Et2O), elem. anal. Quesada, Manuel; De Hoog, Paul; Gamez, Patrick; Roubeau, Olivier; Aromi, Guillem; Donnadieu, Bruno; Massera, Chiara; Lutz, Martin; Spek, Anthony L.; Reedijk, Jan; European Journal of Inorganic Chemistry; nb. 7; (2006); p. 1353 - 1361 ; (from Gmelin) View in Reaxys

(v1) –

F Ag+ F

B– F F

(v3) Au+ (v1)

(v2)

(v3)

(v1) F–

Ag+

(v1) –F F– – –F P5+ F (v1) (v6) (v1) F– (v1)

Au+

(v1)

1.5

N N

(v4)

–F

B3+– – FF

(v1) (v1)

N (v2)

Rx-ID: 27533252 View in Reaxys 174/395 Yield

Conditions & References

57.4 %

in further solvent(s), charging of flask with soln. of (Au(1-methyl-3-(2-pyridinyl)-imidazol-2-ylidene))(PF6) and AgBF4 in PhCH2CN; removal from light; stirring at room temp. for 1.5 h; filtration, concn. under vac., pptn. with Et2O; elem. anal. Catalano, Vincent J.; Etogo, Anthony O.; Journal of Organometallic Chemistry; vol. 690; nb. 24-25; (2005); p. 6041 - 6050 ; (from Gmelin) View in Reaxys

N O

H 2N

NH 2

Rx-ID: 34485738 View in Reaxys 175/395 Yield

Conditions & References With tert -butyl hydrogen peroxide, zinc dibromide in pyridine, water, Time= 16h, T= 80 °C Wu, Xiao-Feng; Bheeter, Charles Beromeo; Neumann, Helfried; Dixneuf, Pierre H.; Beller, Matthias; Chemical Communications; vol. 48; nb. 100; (2012); p. 12237 - 12239 View in Reaxys

Rx-ID: 37302661 View in Reaxys 176/395 Yield Ca. 34 %

Conditions & References T= 800 °C , p= 7.50075E-05 - 0.000750075Torr Begue, Didier; Dargelos, Alain; Berstermann, Hans M.; Netsch, Klaus P.; Bednarek, Pawel; Wentrup, Curt; Journal of Organic Chemistry; vol. 79; nb. 3; (2014); p. 1247 - 1253

65/122

2016-03-14 02:10:57

View in Reaxys

O N

Rx-ID: 669135 View in Reaxys 177/395 Yield

Conditions & References With ammonia, T= 450 - 490 °C , beim leiten ueber Thoriumdioxyd Mailhe; Annales de Chimie (Cachan, France); vol. <9>13; (1920); p. 210; ; vol. 15; p. 9550; Chem. Zentralbl.; vol. 91; nb. I; (1920); p. 115 View in Reaxys Mailhe; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 166; (1918); p. 36; Annales de Chimie (Cachan, France); vol. <9> 13; (1920); p. 218 View in Reaxys

15N

Rx-ID: 2400612 View in Reaxys 178/395 Yield 52 %

Conditions & References in dimethyl sulfoxide, Time= 8h, Ambient temperature Weiner, Scott J.; Holl, Susan M.; Covey, Douglas F.; Magnetic Resonance in Chemistry; vol. 32; nb. 2; (1994); p. 122 - 127 View in Reaxys

H C N

Rx-ID: 2409713 View in Reaxys 179/395 Yield

Conditions & References With tert-butoxyl radical Korth, Hans-Gert; Lommes, Petra; Sicking, Willi; Sustmann, Reiner; Chemische Berichte; vol. 118; nb. 11; (1985); p. 4627 - 4631 View in Reaxys With ammonium cerium(IV) nitrate, benzotriazol-1-ol in acetonitrile, T= 25 °C , Kinetics Brandi, Paolo; Galli, Carlo; Gentili, Patrizia; Journal of Organic Chemistry; vol. 70; nb. 23; (2005); p. 9521 - 9528 View in Reaxys

Rx-ID: 3737402 View in Reaxys 180/395 Yield

Conditions & References

17 %, 79 % With diethylene glycol monoethyl ether, sodium amide in ethylene glycol dimethyl ether, 1.) 45 deg C, 2 h, 2.) -10 deg C, 2 h, 3.) -30 deg C, 14 h Carre, M. C.; Ezzinadi, A. S.; Zouaoui, M. A.; Geoffroy, P.; Caubere, P.; Synthetic Communications; vol. 19; nb. 19; (1989); p. 3323 - 3330 View in Reaxys

66/122

2016-03-14 02:10:57

Rx-ID: 3839156 View in Reaxys 181/395 Yield

Conditions & References

82 %

With tetrachloromethane, 18-crown-6 ether, tributylphosphine in acetonitrile, Time= 3h, Ambient temperature Mizuno, Akira; Hamada, Yasumasa; Shioiri, Takayuki; Synthesis; nb. 12; (1980); p. 1007 - 1009 View in Reaxys

82 %

With tetrachloromethane, 18-crown-6 ether, tributylphosphine in acetonitrile, Time= 3h, Ambient temperature, other phosphines, using CBr4 instead of the CCl4, other reaction times, Product distribution Mizuno, Akira; Hamada, Yasumasa; Shioiri, Takayuki; Synthesis; nb. 12; (1980); p. 1007 - 1009 View in Reaxys

N S

S S

Rx-ID: 5004523 View in Reaxys 182/395 Yield 10 %, 60 %, 11 %

Conditions & References T= 600 °C , p= 0.002Torr Lesniak; Mloston; Heimgartner; Polish Journal of Chemistry; vol. 72; nb. 8; (1998); p. 1915 - 1920 View in Reaxys

10 %, 11 %, 60 %

T= 600 °C , p= 0.002Torr Lesniak; Mloston; Heimgartner; Polish Journal of Chemistry; vol. 72; nb. 8; (1998); p. 1915 - 1920 View in Reaxys

N.N'-dibenzyl-thiourea

Rx-ID: 5589580 View in Reaxys 183/395 Yield

Conditions & References With iron, paraffin oil, T= 280 °C Patent; Bayer and Co.; DE259363; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 204 View in Reaxys

K2<Ni(CN)2(CO)2>, K2<Ni(CN)4>

Rx-ID: 5720780 View in Reaxys 184/395 Yield

Conditions & References

89 %, 6 %, add of carbon monoxide 1% Rosario, R. del; Stuhl, L. S.; Tetrahedron Letters; vol. 23; nb. 39; (1982); p. 3999 - 4002 View in Reaxys

67/122

2016-03-14 02:10:57

6 %, 1 %, 89 %

add of carbon monoxide Rosario, R. del; Stuhl, L. S.; Tetrahedron Letters; vol. 23; nb. 39; (1982); p. 3999 - 4002 View in Reaxys

O O

O S NH O

H 2N

Rx-ID: 37826236 View in Reaxys 185/395 Yield

Conditions & References Reaction Steps: 2 1: methanol / 0.5 h / 65 °C 2: caesium carbonate / acetonitrile / 20 °C With caesium carbonate in methanol, acetonitrile Tang, Hai-Tao; Zhou, Yun-Bing; Zhu, Yu; Sun, Hong-Chao; Lin, Min; Zhan, Zhuang-Ping; Chemistry - An Asian Journal; vol. 9; nb. 5; (2014); p. 1278 - 1281 View in Reaxys

OH N

H 2N

Rx-ID: 539784 View in Reaxys 186/395 Yield

Conditions & References With silica gel, T= 430 - 450 °C Patent; I. G. Farbenind.; DE482943; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 699 View in Reaxys

O Si N

Rx-ID: 2068560 View in Reaxys 187/395 Yield

Conditions & References With P2O5, 1,1,1,3,3,3-hexamethyl-disilazane, sodium iodide, 1) 50 deg C, 1 h, 2) 90 deg C, 10 h, Yield given. Multistep reaction Rao, C. Someswara; Rambabu, M.; Srinivasan, P. S.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 26; nb. 1-12; (1987); p. 407 - 411 View in Reaxys O

H S

Rx-ID: 2679518 View in Reaxys 188/395 Yield

Conditions & References

25 %, 48 % With tributylphosphine Yokoyama, Masataka; Ohteki, Hiroko; Kurauchi, Masahiko; Hoshi, Kazuko; Yanagisawa, Eizaburo; et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 11; (1984); p. 2635 - 2640 View in Reaxys 48 %, 25 % With tributylphosphine

68/122

2016-03-14 02:10:57

Yokoyama, Masataka; Ohteki, Hiroko; Kurauchi, Masahiko; Hoshi, Kazuko; Yanagisawa, Eizaburo; et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 11; (1984); p. 2635 - 2640 View in Reaxys

N 14C

14C

Rx-ID: 2695517 View in Reaxys 189/395 Yield

Conditions & References With 18-crown-6 ether in acetonitrile Jay, Michael; Layton, W. John; Digenis, George A.; Tetrahedron Letters; vol. 21; (1980); p. 2621 - 2624 View in Reaxys

S N

NH 2

Rx-ID: 3929497 View in Reaxys 190/395 Yield

Conditions & References

36 % Chro- With sulfur, ammonia, sodium nitrite, Time= 1h, T= 100 °C mat., 21 % Sato, Ryu; Ityoh, Kaoru; Itoh, Kazumi; Nishina, Hironori; Goto, Takehiko; Saito, Minoru; Chemistry Letters; Chromat. (1984); p. 1913 - 1916 View in Reaxys

–S

Pb N

phenylacetate lead

Rx-ID: 5589581 View in Reaxys 191/395 Yield

Conditions & References bei der Destillation van Epps; Reid; Journal of the American Chemical Society; vol. 38; (1916); p. 2125 View in Reaxys

azide of <3,4-dimethoxy-phenyl>-succinic acid dihydrazide HO

n-hexyl halide Rx-ID: 12157188 View in Reaxys 192/395

Yield

Conditions & References Reaction Steps: 2 1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C 2: 82 percent / 2,6-dimethyl-1,4-benzoquinone / CHCl3 / 24 h / 20 °C With n-butyllithium, 2,6-dimethyl-1,4-benzoquinone in tetrahydrofuran, hexane, chloroform Masutani, Kouta; Minowa, Tomofumi; Hagiwara, Yoshiaki; Mukaiyama, Teruaki; Bulletin of the Chemical Society of Japan; vol. 79; nb. 7; (2006); p. 1106 - 1117 View in Reaxys

69/122

2016-03-14 02:10:57

buten-(1)-oic acid (4)-nitrile

Rx-ID: 15546422 View in Reaxys 193/395 Yield

Conditions & References Reaction Steps: 2 1: 63 percent / pyridine; phosphorus oxychloride / benzene / 20 °C 2: 99 percent / In; aq. sodium dodecyl sulfate / 30 h / 60 °C With pyridine, indium, sodium lauryl sulfate, trichlorophosphate in benzene Park, Leeyoung; Keum, Gyochang; Kang, Soon Bang; Kim, Kwan Soo; Kim, Youseung; Journal of the Chemical Society, Perkin Transactions 1; nb. 24; (2000); p. 4462 - 4463 View in Reaxys

(C5H5)2(Cl)Zr{trans-CH=CH[CH2]4OSi(CH3)2(tBu)}

buten-(1)-oic acid (4)-nitrile

Rx-ID: 15551498 View in Reaxys 194/395 Yield

Conditions & References Reaction Steps: 3 1: 70 percent / sodium bisulfite / H2O / 6 h / 20 °C 2: 63 percent / pyridine; phosphorus oxychloride / benzene / 20 °C 3: 99 percent / In; aq. sodium dodecyl sulfate / 30 h / 60 °C With pyridine, indium, sodium lauryl sulfate, sodium hydrogensulfite, trichlorophosphate in water, benzene Park, Leeyoung; Keum, Gyochang; Kang, Soon Bang; Kim, Kwan Soo; Kim, Youseung; Journal of the Chemical Society, Perkin Transactions 1; nb. 24; (2000); p. 4462 - 4463 View in Reaxys

alcoholic potash

disulfur dichloride

Rx-ID: 20557634 View in Reaxys 195/395 Yield

Conditions & References Reaction Steps: 2 1: 59 percent / K2CO3, 18-crown-6-ether / acetonitrile / 28 h / Heating 2: 81.3 percent / dimethylsulfoxide / 6 h With 18-crown-6 ether, potassium carbonate in dimethyl sulfoxide, acetonitrile Julia, Louis; Suschitzky, H.; Barnes, John C.; Tomlin, Clive D.S.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 10; (1983); p. 2507 - 2511 View in Reaxys H C–

H S

HS( 1-)

Rx-ID: 26170786 View in Reaxys 196/395 Yield

Conditions & References equil. react.; reaction studied by ICR technique at 298 K vol. S: SVol.4a/b; 1.3.8.11.3, page 217 - 219 ; (from Gmelin) View in Reaxys equil. react.; reaction studied by ICR technique at 298 K

70/122

2016-03-14 02:10:57

Bartmess et al.; Journal of the American Chemical Society; vol. 101; (1979); p. 6046,6049,6053 ; (from Gmelin) View in Reaxys

potassium cyanide supported on alumi‐ na

Rx-ID: 31847453 View in Reaxys 197/395 Yield

Conditions & References

79 %Chromat.

With toluene, Time= 24h, T= 50 °C , Sonication Doan, Tan L.H.; Le, Thach N.; Synthetic Communications; vol. 42; nb. 3; (2012); p. 337 - 340 View in Reaxys

Rx-ID: 34038583 View in Reaxys 198/395 Yield

Conditions & References Reaction Steps: 2 1.1: copper (I) cyanide / tetrahydrofuran; hexane; diethyl ether / 0.17 h / -30 - -10 °C / |Inert atmosphere 1.2: 0.33 h / -30 °C / |Inert atmosphere 1.3: -30 °C / |Inert atmosphere 2.1: dicyclohexyl-carbodiimide; pyridine; triethylamine / tetrahydrofuran; hexane; diethyl ether; dichloromethane / 12 h / 20 °C / |Inert atmosphere With pyridine, copper (I) cyanide, triethylamine, dicyclohexyl-carbodiimide in tetrahydrofuran, diethyl ether, hexane, dichloromethane Sengupta, Ritobroto; Weinreb, Steven M.; Synthesis (Germany); vol. 44; nb. 18; (2012); p. 2933 - 2937 View in Reaxys

Rx-ID: 37685371 View in Reaxys 199/395 Yield

Conditions & References Reaction Steps: 2 1: iodine / water / 20 °C / |Green chemistry 2: ammonia / water / 20 °C / |Green chemistry With ammonia, iodine in water Yadav, Arvind K.; Srivastava, Vishnu P.; Yadav, Lal Dhar S.; Synthetic Communications; vol. 44; nb. 3; (2014); p. 408 - 416 View in Reaxys 2H

2H 2H

N 2H

Br 2H

2H 2H

Rx-ID: 39808846 View in Reaxys 200/395 Yield

Conditions & References Reaction Steps: 2 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / |Inert atmosphere 1.2: 0.5 h / -78 °C / |Inert atmosphere 2.1: Ni(acac)2; triphenylphosphine; potassium phosphate / toluene / 3 h / 80 °C / |Inert atmosphere With potassium phosphate, n-butyllithium, Ni(acac)2, triphenylphosphine in tetrahydrofuran, hexane, toluene

71/122

2016-03-14 02:10:57

Takamatsu, Kazutaka; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3242 - 3249 View in Reaxys

N O

Rx-ID: 41494859 View in Reaxys 201/395 Yield

Conditions & References Reaction Steps: 2 1: ammonium hydroxide / water / 16 h / 20 °C / |Inert atmosphere 2: Xtalfluor-E®; triethylamine / ethyl acetate / 1 h / 20 °C / |Inert atmosphere With ammonium hydroxide, triethylamine, Xtalfluor-E® in water, ethyl acetate Keita, Massaba; Vandamme, Mathilde; Paquin, Jean-Franois; Synthesis (Germany); vol. 47; nb. 23; (2015); p. 3758 - 3766; Art.No: SS-2015-M0394-OP View in Reaxys OH

Rx-ID: 332823 View in Reaxys 202/395 Yield

Conditions & References With platinum on activated charcoal, ethanol, Hydrogenation Zelinsky; Packendorff; Leder-Packendorff; Chemische Berichte; vol. 67; (1934); p. 300 View in Reaxys With ethanol, hydrazine hydrate Purgotti; Gazzetta Chimica Italiana; vol. 25 I; (1895); p. 120 View in Reaxys Reaction Steps: 2 1: chloroform; thionyl chloride / 0 °C 2: ethanol; zinc-powder; aqueous acetic acid With thionyl chloride, ethanol, chloroform, acetic acid, zinc Hignett; Kay; Journal of the Society of Chemical Industry, London; vol. 54; (1935); p. 98 T View in Reaxys

HO N S

Rx-ID: 357606 View in Reaxys 203/395 Yield

Conditions & References With pyridine, hydroxylamine hydrochloride, T= 75 °C Wuyts; Bulletin des Societes Chimiques Belges; vol. 39; (1930); p. 58,63 View in Reaxys

Rx-ID: 816983 View in Reaxys 204/395 Yield

Conditions & References With copper(l) chloride, T= 80 - 100 °C

72/122

2016-03-14 02:10:57

Kurtz in K. Ziegler; View in Reaxys O S N

O N

Rx-ID: 2135992 View in Reaxys 205/395 Yield

Conditions & References

86 % Chro- With sodium methylate in methanol, Time= 0.166667h, T= 60 °C mat. Jarvis, Bruce B.; Nicholas, Paul, E.; Journal of Organic Chemistry; vol. 45; nb. 11; (1980); p. 2265 - 2268 View in Reaxys 2H

2H 2H

C–

N+

Rx-ID: 4674949 View in Reaxys 206/395 Yield

Conditions & References in water, dimethyl sulfoxide, T= 30 °C , secondary α deuterium kinetic isotope effects for the SN2 reactions between psubstituted benzyl chlorides and cyanide ion, Rate constant Westaway, Kenneth Charles; Van Pham, Thuy; Fang, Yao-Ren; Journal of the American Chemical Society; vol. 119; nb. 16; (1997); p. 3670 - 3676 View in Reaxys

N 14C

14C

Rx-ID: 10413134 View in Reaxys 207/395 Yield

Conditions & References With tetrabutylammomium bromide in water, Time= 0.0666667h, microwave irradiation Mathew; Ravi; Unny; Sivaprasad; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 8; (2006); p. 699 - 705 View in Reaxys

–C

K+

Rx-ID: 11051476 View in Reaxys 208/395 Yield

Conditions & References in water, dimethyl sulfoxide, T= 40 °C , Kinetics, Further Variations: Solvents Vinci; Donaldson; Hallett; John; Pollet; Thomas; Grilly; Jessop; Liotta; Eckert; Chemical Communications; nb. 14; (2007); p. 1427 - 1429 View in Reaxys

98.9 With C58H82N4O8 in dimethyl sulfoxide, Time= 24h, T= 40 °C %Chromat. Yang, Fafu; Wang, Yanhua; Guo, Hongyu; Xie, Jianwei; Liu, Zhiqiang; Canadian Journal of Chemistry; vol. 88; nb. 7; (2010); p. 622 - 627 View in Reaxys 96.6 With 2Br(1-)*C64H90N4O4 (2+) in water, Time= 12h, T= 50 °C %Chromat. Yang, Fafu; Guo, Hongyu; Jiao, Ziyu; Li, Congcong; Ye, Jinqi; Journal of the Iranian Chemical Society; vol. 9; nb. 3; (2012); p. 327 - 332

73/122

2016-03-14 02:10:57

View in Reaxys

(v3) (v3)

O O (v6) Co 3O O

(v3) (v3)

O (v3)

Rx-ID: 26733717 View in Reaxys 209/395 Yield

Conditions & References in not given, acidic soln.; Kwiatek, J.; Seyler, J. K.; Journal of Organometallic Chemistry; vol. 3; (1965); p. 433 - 437 ; (from Gmelin) View in Reaxys in not given, acidic soln.; vol. Co: Org.Verb.1; 1.1.3.1.1.2, page 58 - 65 ; (from Gmelin) View in Reaxys

N N

N OH N

–

BH– N

2 Cl –

Rh 3+

Rx-ID: 26755751 View in Reaxys 210/395 Yield

Conditions & References in toluene, refluxing under nitrogen May, S. M.; Reinsalu, P.; Powell, J.; Inorganic Chemistry; vol. 19; (1980); p. 1582 - 1589 View in Reaxys vol. Rh: SVol.B2; 2.6.1, page 239 - 240 ; (from Gmelin) View in Reaxys

N N

Rx-ID: 28676539 View in Reaxys 211/395 Yield

Conditions & References With triethylamine in chloroform Rao, H. Surya Prakash; Padmavathy; Vasantham; Rafi, Shaik; Synthetic Communications; vol. 39; nb. 10; (2009); p. 1825 - 1834 View in Reaxys

Rx-ID: 37302659 View in Reaxys 212/395 Yield

Conditions & References T= 850 °C , p= 7.50075E-05 - 0.000750075Torr Begue, Didier; Dargelos, Alain; Berstermann, Hans M.; Netsch, Klaus P.; Bednarek, Pawel; Wentrup, Curt; Journal of Organic Chemistry; vol. 79; nb. 3; (2014); p. 1247 - 1253 View in Reaxys

74/122

2016-03-14 02:10:57

Rx-ID: 2256942 View in Reaxys 213/395 Yield

Conditions & References in ethanol Chao, Herbert S.-I.; Berchtold, Glenn A.; Journal of Organic Chemistry; vol. 46; nb. 6; (1981); p. 1191 - 1194 View in Reaxys

O O

H N N N N

N O O

Rx-ID: 3165248 View in Reaxys 214/395 Yield

Conditions & References

77 %, 15 % With sodium methylate in ethanol, Time= 3h, Heating, Product distribution Neunhoeffer, Hans; Diehl, Werner; Karafiat, Ute; Liebigs Annalen der Chemie; (1989); p. 105 - 110 View in Reaxys

Rx-ID: 5149994 View in Reaxys 215/395 Yield

Conditions & References With tetrabutyl ammonium fluoride in acetonitrile, Time= 1h, T= 25 °C , other reagent, temperature, reaction time, Product distribution Soli, Eric D.; Manoso, Amy S.; Patterson, Michael C.; DeShong, Philip; Favor, David A.; Hirschmann, Ralph; Smith III, Amos B.; Journal of Organic Chemistry; vol. 64; nb. 9; (1999); p. 3171 - 3177 View in Reaxys

Si N

Rx-ID: 5152031 View in Reaxys 216/395 Yield

Conditions & References With tetrabutyl ammonium fluoride in acetonitrile, Time= 72h, T= 25 °C , other temperature, reaction time, Product distribution Soli, Eric D.; Manoso, Amy S.; Patterson, Michael C.; DeShong, Philip; Favor, David A.; Hirschmann, Ralph; Smith III, Amos B.; Journal of Organic Chemistry; vol. 64; nb. 9; (1999); p. 3171 - 3177 View in Reaxys

(C6H5CC)2CuLi (6s)

Rx-ID: 5589577 View in Reaxys 217/395 Yield

Conditions & References With hydrogenchloride, O-(diphenyl-phosphinyl)hydroxylamine, Yield given. Multistep reaction

75/122

2016-03-14 02:10:57

Boche, Gernot; Bernheim, Michael; Schrott, Wolfgang; Tetrahedron Letters; vol. 23; nb. 51; (1982); p. 5399 - 5402 View in Reaxys

Br B

CH 2

Rx-ID: 26159176 View in Reaxys 218/395 Yield

Conditions & References in carbon disulfide Johnson, A. R.; Journal of Physical Chemistry; vol. 16; (1912); p. 1 ; (from Gmelin) View in Reaxys in tetrachloromethane Johnson, A. R.; Journal of Physical Chemistry; vol. 16; (1912); p. 1 ; (from Gmelin) View in Reaxys in carbon disulfide vol. B: MVol.; 10.1.3, page 125 - 126 ; (from Gmelin) View in Reaxys in tetrachloromethane vol. B: MVol.; 10.1.3, page 125 - 126 ; (from Gmelin) View in Reaxys 3 Cl – Cl (v4) N N (v4)

Rh 3+

(v6)(v4) Cl

Rh N OC-6

2 Cl

Rx-ID: 26758587 View in Reaxys 219/395 Yield

Conditions & References in toluene, reflux for 1h Gillard, R. D.; Heaton, B. T.; Shaw, H.; Inorganica Chimica Acta; vol. 7; (1973); p. 102 - 104 View in Reaxys vol. Rh: SVol.B2; 2.1.4.7, page 123 - 123 ; (from Gmelin) View in Reaxys O–

Cl O OO (v3)

O– (v4)

3 (v4) (v4)

(v4) NH 3 3+

H 3N Rh NH 3 (v6) H N (v4) 3 NH 3

OH 2

(v6) H 3N NH 3+ H N Rh NH33 Cl (v4) OO 3 NH 3

(v4)

Rx-ID: 27072991 View in Reaxys 220/395 Yield

Conditions & References in water, Irradiation (UV/VIS); photolyses in room temp. aq. soln. at 313 or 254 nm Bergkamp, Michael A.; Watts, Richard J.; Ford, Peter C.; Inorganic Chemistry; vol. 20; (1981); p. 1764 - 1767 ; (from Gmelin) View in Reaxys

76/122

2016-03-14 02:10:57

Rx-ID: 37302660 View in Reaxys 221/395 Yield

Conditions & References T= 700 °C , p= 7.50075E-05 - 0.000750075Torr Begue, Didier; Dargelos, Alain; Berstermann, Hans M.; Netsch, Klaus P.; Bednarek, Pawel; Wentrup, Curt; Journal of Organic Chemistry; vol. 79; nb. 3; (2014); p. 1247 - 1253 View in Reaxys

H N N N N

H racemate

Rx-ID: 3256089 View in Reaxys 222/395 Yield

Conditions & References

66 % T= 400 °C , p= 0.01Torr Spectr., 49 % Spectr. Hoffmann, Reinhard W.; Barth, Wolfgang; Chemische Berichte; vol. 118; nb. 2; (1985); p. 634 - 642 View in Reaxys

ammonium-<phenylacetyl-amido sul‐ fate>

Rx-ID: 5589576 View in Reaxys 223/395 Yield

Conditions & References T= 180 °C Gagnon et al.; Canadian Journal of Chemistry; vol. 34; (1956); p. 1662,1666 View in Reaxys

ClCN

Rx-ID: 5589578 View in Reaxys 224/395 Yield

Conditions & References T= 600 - 700 °C Patent; Am. Cyanamid Co.; US2606917; (1951) View in Reaxys Patent; Am. Cyanamid Co.; US2553404; (1950) View in Reaxys Patent; Am. Cyanamid Co.; DE848358; (1951); View in Reaxys

Cl N

(v5)

Cl 2

Cl O

N (v5)

Rx-ID: 26600600 View in Reaxys 225/395 Yield

Conditions & References in tetrachloromethane, addition of a solution of C6H5CH2CN in CCl4 drop by drop to a solution of VOCl3 in CCl4 under exclusion of H2O; Funk, H.; Weiss, W.; Zeising, M.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 296; (1958); p. 36 - 45 ; (from Gmelin)

77/122

2016-03-14 02:10:57

View in Reaxys in tetrachloromethane, addition of a solution of C6H5CH2CN in CCl4 drop by drop to a solution of VOCl3 in CCl4 under exclusion of H2O; vol. V: MVol.B2; 209, page 817 - 819 ; (from Gmelin) View in Reaxys

Cl Cl

(v4)

V ClCl

(v4)

V ClCl

Rx-ID: 26607967 View in Reaxys 226/395 Yield

Conditions & References in tetrachloromethane, dropwise addition of a solution of 1 ml VCl in 2 ml CCl4 to a solution of 2.5 g benzylcyanide in 15 ml CCl4 under N2;; washing with CCl4 or hexane; Funk, H.; Mohaupt, G.; Paul, A.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 302; (1959); p. 199 210 ; (from Gmelin) View in Reaxys in tetrachloromethane, dropwise addition of a solution of 1 ml VCl in 2 ml CCl4 to a solution of 2.5 g benzylcyanide in 15 ml CCl4 under N2;; washing with CCl4 or hexane; vol. V: MVol.B2; 193, page 783 - 784 ; (from Gmelin) View in Reaxys

O O

Rx-ID: 37302654 View in Reaxys 227/395 Yield

N H 2N

Rx-ID: 269362 View in Reaxys 228/395 Yield

Conditions & References With methanol, sodium hypochlorite Rinkes; Recueil des Travaux Chimiques des Pays-Bas; vol. 39; (1920); p. 707 View in Reaxys Reaction Steps: 2 1: sodium hypochlorite 2: aq. barium hydroxide solution / Destillieren des Reaktionsprodukts mit Wasserdampf With barium dihydroxide, sodium hypochlorite Rinkes; Recueil des Travaux Chimiques des Pays-Bas; vol. 39; (1920); p. 707 View in Reaxys

78/122

2016-03-14 02:10:57

H N HO

Rx-ID: 2068152 View in Reaxys 229/395 Yield

Conditions & References With bis(trimethylsilyl)-sulfide, potassium hydride, 1) THF, 0 deg C, 30 min, then rt, 1 h, 2) rt, 24 h, then reflux, 48 h, Yield given. Multistep reaction. Yields of byproduct given Hwu, Jih Ru; Tsay, Shwu-Chen; Tetrahedron; vol. 46; nb. 21; (1990); p. 7413 - 7428 View in Reaxys

Rx-ID: 2677737 View in Reaxys 230/395 Yield

Conditions & References

47 %, 35 % With tributylphosphine, 1.) 1h, 0 deg C, 2.) 2h, ambient temperature Kurauchi, Masahiko; Imamoto, Tsuneo; Yokoyama, Masataka; Tetrahedron Letters; vol. 22; nb. 49; (1981); p. 4985 - 4986 View in Reaxys 47 %, 35 % With tributylphosphine, 1.) 0 deg C, 1 h, 2.) room temperature, 2 h Yokoyama, Masataka; Ohteki, Hiroko; Kurauchi, Masahiko; Hoshi, Kazuko; Yanagisawa, Eizaburo; et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 11; (1984); p. 2635 - 2640 View in Reaxys 47 %, 35 % With tributylphosphine, 1.) 1h, 0 deg C, 2.) 2h , ambient temperature; investigation of reactions of various aromatic aldehydes, Product distribution Kurauchi, Masahiko; Imamoto, Tsuneo; Yokoyama, Masataka; Tetrahedron Letters; vol. 22; nb. 49; (1981); p. 4985 - 4986 View in Reaxys 35 %, 47 % With tributylphosphine, 1.) 1h, 0 deg C, 2.) 2h, ambient temperature Kurauchi, Masahiko; Imamoto, Tsuneo; Yokoyama, Masataka; Tetrahedron Letters; vol. 22; nb. 49; (1981); p. 4985 - 4986 View in Reaxys 35 %, 47 % With tributylphosphine, 1.) 0 deg C, 1 h, 2.) room temperature, 2 h Yokoyama, Masataka; Ohteki, Hiroko; Kurauchi, Masahiko; Hoshi, Kazuko; Yanagisawa, Eizaburo; et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 11; (1984); p. 2635 - 2640 View in Reaxys

H N

Rx-ID: 2684364 View in Reaxys 231/395 Yield

Conditions & References With Macroreticular St-DVB copolymer, 1.) EtOH, reflux, 0.5 h, 2.) MeOH, reflux, 72 h, Yield given. Multistep reaction Kamogawa, Hiroyoshi; Kanzawa, Asami; Kadoya, Masahiro; Naito, Takeshi; Nanasawa, Masato; Bulletin of the Chemical Society of Japan; vol. 56; nb. 3; (1983); p. 762 - 765 View in Reaxys

79/122

2016-03-14 02:10:57

Rx-ID: 2695331 View in Reaxys 232/395 Yield

Conditions & References in tetrahydrofuran, Time= 6h, Heating, Yield given Harusawa, Shinya; Yoneda, Ryuji; Omori, Yukie; Kurihara, Takushi; Tetrahedron Letters; vol. 28; nb. 36; (1987); p. 4189 - 4190 View in Reaxys H N

Rx-ID: 3737359 View in Reaxys 233/395 Yield 63 %, 8 %

Conditions & References Heating, Title compound not separated from byproducts Polivin, Yu. N.; Vinokurov, V. A.; Makarshin, S. V.; Karakhanov, R. A.; Silin, M. A.; Ageev, E. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 39; nb. 7.2; (1990); p. 1528 - 1530; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 7; (1990); p. 1682 - 1684 View in Reaxys

8 %, 63 %

Heating, Title compound not separated from byproducts Polivin, Yu. N.; Vinokurov, V. A.; Makarshin, S. V.; Karakhanov, R. A.; Silin, M. A.; Ageev, E. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 39; nb. 7.2; (1990); p. 1528 - 1530; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 7; (1990); p. 1682 - 1684 View in Reaxys H C–

Rx-ID: 4082249 View in Reaxys 234/395 Yield

Conditions & References With methanol, sodium methylate, dimethyl sulfoxide Binev, I. G.; Tsenov, J. A.; Velcheva, E. A.; Juchnovski, I. N.; Journal of Molecular Structure; vol. 344; (1995); p. 205 - 216 View in Reaxys

(+-)-acetoxy-phenyl-acetonitrile

Rx-ID: 5589575 View in Reaxys 235/395 Yield

Conditions & References With methanol, palladium on activated charcoal, Hydrogenation Kindler; Schrader; Justus Liebigs Annalen der Chemie; vol. 564; (1949); p. 49,51, 52 View in Reaxys

phenylpropiolic acid amide ox‐ ime

Rx-ID: 5589582 View in Reaxys 236/395 Yield

Conditions & References With iodine, sodium carbonate

80/122

2016-03-14 02:10:57

Robin; Annales de Chimie (Cachan, France); vol. <9> 16; (1921); p. 120 View in Reaxys

Rx-ID: 8673452 View in Reaxys 237/395 Yield

Conditions & References

10 %, 8 %, T= 1000 °C , Formation of xenobiotics, vacuum flash pyrolysis, Further byproducts given. Title compound not separated 3 %, 4.5 % from byproducts Banciu, Mircea D.; Istrati, Daniela; Mihaiescu, Dan; Draghici, Constantin; Molecules; vol. 5; nb. 8; (2000); p. 1004 - 1010 View in Reaxys

N O

O N

Rx-ID: 9088503 View in Reaxys 238/395 Yield 13 % Chromat., 16 % Chromat., 54 % Chromat.

Conditions & References With potassium carbonate in methanol, Time= 150h, T= 140 °C , Product distribution, Kinetics, Further Variations: time Tundo, Pietro; Selva, Maurizio; Perosa, Alvise; Memoli, Sofia; Journal of Organic Chemistry; vol. 67; nb. 4; (2002); p. 1071 - 1077 View in Reaxys 1

Rx-ID: 9138460 View in Reaxys 239/395 Yield

Conditions & References With tert-butoxyl radical in benzene, Kinetics Font-Sanchis, Enrique; Aliaga, Carolina; Focsaneanu; Scaiano; Chemical Communications; nb. 15; (2002); p. 1576 - 1577 View in Reaxys

Cl N

Rx-ID: 21988493 View in Reaxys 240/395 Yield

Conditions & References Reaction Steps: 3 1: benzene; ammonia 2: sodium hypochlorite 3: aq. barium hydroxide solution / Destillieren des Reaktionsprodukts mit Wasserdampf With barium dihydroxide, sodium hypochlorite, ammonia, benzene Rinkes; Recueil des Travaux Chimiques des Pays-Bas; vol. 39; (1920); p. 707 View in Reaxys Reaction Steps: 2 1: benzene; ammonia

81/122

2016-03-14 02:10:57

2: methanol; sodium hypochlorite With methanol, sodium hypochlorite, ammonia, benzene Rinkes; Recueil des Travaux Chimiques des Pays-Bas; vol. 39; (1920); p. 707 View in Reaxys

ClCu

Rx-ID: 26561774 View in Reaxys 241/395 Yield

Conditions & References in hydrogenchloride Rabaut, C.; Bulletin de la Societe Chimique de France; vol. 19; (1898); p. 785 - 788 ; (from Gmelin) View in Reaxys in hydrogenchloride vol. Cu: MVol.B1; 111, page 242 - 244 ; (from Gmelin) View in Reaxys

ClCu

Rx-ID: 26648007 View in Reaxys 242/395 Yield

Conditions & References in sodium hydroxide Rabaut, C.; Bulletin de la Societe Chimique de France; vol. 19; (1898); p. 785 - 788 ; (from Gmelin) View in Reaxys in sodium hydroxide, aq. NaOH vol. Cu: MVol.B1; 111, page 242 - 244 ; (from Gmelin) View in Reaxys

(v2)

OH –

(v5)

Cl NbCl Cl N

H O

(v1)

(v5) Cl5+ – (v1) –Cl NbCl – (v1) – Cl (v1)

Rx-ID: 27318301 View in Reaxys 243/395 Yield

Conditions & References in acetonitrile-D3, (N2) Lee, G. Robert; Crayston, Joe A.; Polyhedron; vol. 15; nb. 11; (1996); p. 1817 - 1821 ; (from Gmelin) View in Reaxys

ClCl (v2) ClCl Nb Cl Cl (v6) Nb ClCl (v6) (v2) ClCl

Cl (v5)

Cl NbCl Cl

Rx-ID: 27347358 View in Reaxys 244/395 Yield

Conditions & References in further solvent(s), Sonication; (N2); 60°C, 1 h; solvent removal Lee, G. Robert; Crayston, Joe A.; Polyhedron; vol. 15; nb. 11; (1996); p. 1817 - 1821 ; (from Gmelin) View in Reaxys

82/122

2016-03-14 02:10:57

–C

K+

Rx-ID: 31847452 View in Reaxys 245/395 Yield

Conditions & References

19 %Chromat.

With aluminum oxide, Time= 24h, T= 50 °C , Sonication Doan, Tan L.H.; Le, Thach N.; Synthetic Communications; vol. 42; nb. 3; (2012); p. 337 - 340 View in Reaxys

O H 2N

Rx-ID: 67142 View in Reaxys 246/395 Yield

Conditions & References T= 225 °C Oxley et al.; Journal of the Chemical Society; (1946); p. 763,766 View in Reaxys

NH N

Rx-ID: 416948 View in Reaxys 247/395 Yield

Conditions & References With barium dihydroxide, Destillieren des Reaktionsprodukts mit Wasserdampf Rinkes; Recueil des Travaux Chimiques des Pays-Bas; vol. 39; (1920); p. 707 View in Reaxys

F B

Rx-ID: 578219 View in Reaxys 248/395 Yield

Conditions & References With boron trifluoride Patein; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 113; (1891); p. 86 View in Reaxys 3H

Rx-ID: 2036319 View in Reaxys 249/395 Yield

Conditions & References With piperidine in dimethyl sulfoxide, T= 25 °C , other aliphatic amines and guanidines; other temperature; ΔH(excit.), ΔS(excit.), Thermodynamic data, Kinetics, Mechanism Bowden, Keith; Madvi, Nighat S.; Ranson, Richard J.; Journal of Chemical Research, Miniprint; nb. 10; (1990); p. 2474 - 2496 View in Reaxys

83/122

2016-03-14 02:10:57

O NH 2

N O

Rx-ID: 2091162 View in Reaxys 250/395 Yield

Conditions & References

23 %, 13 % With iodosylbenzene in dichloromethane, Time= 0.5h, Ambient temperature Mueller, Paul; Gilabert, David Manuel; Tetrahedron; vol. 44; nb. 23; (1988); p. 7171 - 7176 View in Reaxys With iodosylbenzene in dichloromethane, Time= 0.5h, Ambient temperature, with/without molecular sieves (4 A), Product distribution Mueller, Paul; Gilabert, David Manuel; Tetrahedron; vol. 44; nb. 23; (1988); p. 7171 - 7176 View in Reaxys 2H

Rx-ID: 2116124 View in Reaxys 251/395 Yield

Conditions & References With piperidine in dimethyl sulfoxide, T= 25 °C , Rate constant Bowden, Keith; Madvi, Nighat S.; Ranson, Richard J.; Journal of Chemical Research, Miniprint; nb. 10; (1990); p. 2474 - 2496 View in Reaxys

–O

H N K+

Rx-ID: 2762542 View in Reaxys 252/395 Yield

Conditions & References With hydrogenchloride, 1) water, 0 deg C, 2) daylight, 3 h, Yield given. Multistep reaction Tsay, Shwu-Chen; Gani, Paul; Hwu, Jih Ru; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 6; (1991); p. 1493 - 1495 View in Reaxys O O

NE N

Rx-ID: 2816110 View in Reaxys 253/395 Yield

Conditions & References With base in 1,4-dioxane, water, T= 25 °C , pH: 10.25-13.0, solvent 7:3 water-dioxan, ionic strength: 1.0 (NaCl)., Rate constant Hegarty, Anthony F.; Tuohey, Patrick J.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1980); p. 1313 - 1317 View in Reaxys 2H

C–

Li+

Rx-ID: 3169889 View in Reaxys 254/395

84/122

2016-03-14 02:10:57

Yield

Conditions & References With water-d2 Zarges, Wolfgang; Marsch, Michael; Harms, Klaus; Boche, Gernot; Angewandte Chemie; vol. 101; nb. 10; (1989); p. 1424 - 1425 View in Reaxys

N– 2

N N

N–

H C–

Li+

Rx-ID: 3184833 View in Reaxys 255/395 Yield

Conditions & References With water-d2 Zarges, Wolfgang; Marsch, Michael; Harms, Klaus; Boche, Gernot; Angewandte Chemie; vol. 101; nb. 10; (1989); p. 1424 - 1425 View in Reaxys

O NH 2

graphite

Rx-ID: 5818181 View in Reaxys 256/395 Yield

Conditions & References T= 250 - 260 °C Boehner; Andrews; Journal of the American Chemical Society; vol. 38; (1916); p. 2504 View in Reaxys

Br N

HO O

Rx-ID: 21068374 View in Reaxys 257/395 Yield

Conditions & References Reaction Steps: 2 1: 38 percent / heptane / Heating 2: 8 percent / Heating in n-heptane Polivin, Yu. N.; Vinokurov, V. A.; Makarshin, S. V.; Karakhanov, R. A.; Silin, M. A.; Ageev, E. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 39; nb. 7.2; (1990); p. 1528 - 1530; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 7; (1990); p. 1682 - 1684 View in Reaxys

H 2N

N O

Rx-ID: 22296493 View in Reaxys 258/395 Yield

Conditions & References Reaction Steps: 2 1: alcohol; hydrochloric acid; sodium nitrite With hydrogenchloride, ethanol, sodium nitrite Curtius; Kenngott; Journal fuer Praktische Chemie (Leipzig); vol. <2> 112; (1926); p. 325 View in Reaxys

85/122

2016-03-14 02:10:57

Rx-ID: 22315213 View in Reaxys 259/395 Yield

Conditions & References Reaction Steps: 3 1: hydrazine hydrate / -20 °C 2: alcohol; hydrochloric acid; sodium nitrite With hydrogenchloride, ethanol, hydrazine hydrate, sodium nitrite Curtius; Kenngott; Journal fuer Praktische Chemie (Leipzig); vol. <2> 112; (1926); p. 325 View in Reaxys

N+ N

Cl –

Rx-ID: 589148 View in Reaxys 260/395 Yield

Conditions & References T= 130 - 230 °C v. Meyer; Chem. Zentralbl.; vol. 80; nb. II; (1909); p. 1801 View in Reaxys

H H 2N

Rx-ID: 2020882 View in Reaxys 261/395 Yield

Conditions & References With hydrogenchloride, chloramine-T in water, T= 29.9 - 39.9 °C , Ea, log A, -ΔS(excit.), ΔH(excit.), ΔG(excit.); in alkaline media, Thermodynamic data, Rate constant Gowda, Basavalinganadoddy Thimme; Mahadevappa, Darndinasivara S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 323 - 334 View in Reaxys

NH 2

N NH 2

H 2N

NH 2

Rx-ID: 2542019 View in Reaxys 262/395 Yield

Conditions & References

10 %, 10 With ammonia, KNH2, Time= 0.0333333h %, 5 %, 10 Streef, J. W.; Hertog, H. J. den; Plas, H. C. van der; Journal of Heterocyclic Chemistry; vol. 22; (1985); p. 985 - 991 % View in Reaxys

OH N

Rx-ID: 3350210 View in Reaxys 263/395 Yield

Conditions & References With triphenylphosphine, diethylazodicarboxylate, 1.) ether, 0 deg C, 10 min, 2.) ether, a) 0 deg C, 5 min, b) RT, 10 min, Yield given. Multistep reaction Wilk; Synthetic Communications; vol. 23; nb. 17; (1993); p. 2481 - 2484

86/122

2016-03-14 02:10:57

View in Reaxys

Br N

HO O

Rx-ID: 3737397 View in Reaxys 264/395 Yield

Conditions & References T= 200 °C Polivin, Yu. N.; Vinokurov, V. A.; Makarshin, S. V.; Karakhanov, R. A.; Silin, M. A.; Ageev, E. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 39; nb. 7.2; (1990); p. 1528 - 1530; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 7; (1990); p. 1682 - 1684 View in Reaxys

C–

N+

Rx-ID: 5330289 View in Reaxys 265/395 Yield

Conditions & References With tetra-n-butylammonium tetrafluoroborate in acetonitrile-D3, T= 20 °C , Substitution, Kinetics, Further Variations: Solvents Daasbjerg, Kim; Knudsen, Stig R.; Sonnichsen, Katrine N.; Andrade, Adalgisa R.; Pedersen, Steen U.; Acta Chemica Scandinavica; vol. 53; nb. 10; (1999); p. 938 - 948 View in Reaxys

HC N

Rx-ID: 5734096 View in Reaxys 266/395 Yield

Conditions & References T= 946.9 °C Bock, Hans; Wittmann, Joerg; Arpe, Hans-Juergen; Chemische Berichte; vol. 115; nb. 6; (1982); p. 2326 - 2337 View in Reaxys

O HO

CO2

H 2N

Rx-ID: 7452253 View in Reaxys 267/395 Yield

Conditions & References With perchloric acid, chloramine-T in water, T= 29.9 °C , E(activ.), ΔG(excit.), ΔH(excit.), ΔS(excit.); also in the presence of Cl(-); other temperatures and solvent, effect of acid concentration, Kinetics, Mechanism, Thermodynamic data Gowda, B. Thimme; Rao, R. Vijayalakshmi; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical; vol. 27; nb. 1; (1988); p. 39 - 43 View in Reaxys

87/122

2016-03-14 02:10:57

NH N

Rx-ID: 8807540 View in Reaxys 268/395 Yield

Conditions & References

10 %, 1 %, With ZCOY-7 zeolite, T= 450 °C , Product distribution, Further Variations: Reagents, Temperatures 38 % Moyano; Yranzo; Journal of Organic Chemistry; vol. 66; nb. 9; (2001); p. 2943 - 2947 View in Reaxys

Rx-ID: 9077383 View in Reaxys 269/395 Yield

Conditions & References

66 % Chro- With potassium carbonate in N,N-dimethyl-formamide, Time= 0.166667h, T= 150 °C , Product distribution, Further mat., 24 % Variations: Temperatures, reaction times Chromat. Perosa, Alvise; Selva, Maurizio; Tundo, Pietro; Journal of the Chemical Society, Perkin Transactions 2; nb. 5; (2002); p. 1033 - 1037 View in Reaxys

Rx-ID: 35316961 View in Reaxys 270/395 Yield

Conditions & References

0.22 %

, Time= 3h, Irradiation, Wavelength Yoshida, Hisao; Fujimura, Yuki; Yuzawa, Hayato; Kumagai, Jun; Yoshida, Tomoko; Chemical Communications; vol. 49; nb. 36; (2013); p. 3793 - 3795 View in Reaxys

0.32 %

, Time= 3h, Irradiation Yoshida, Hisao; Fujimura, Yuki; Yuzawa, Hayato; Kumagai, Jun; Yoshida, Tomoko; Chemical Communications; vol. 49; nb. 36; (2013); p. 3793 - 3795 View in Reaxys

O N

Rx-ID: 2396902 View in Reaxys 271/395 Yield 55 % Chromat., 5.0 % Chromat., 5.8 % Chromat.

Conditions & References With aluminum oxide in water, toluene, T= 50 °C , Irradiation, various amount of water and time, Product distribution Ando, Takashi; Kawate, Takehiko; Ichihara, Junko (nee Yamawaki); Hanafusa, Terukiyo; Chemistry Letters; (1984); p. 725 - 728 View in Reaxys

88/122

2016-03-14 02:10:57

O O

Rx-ID: 2409472 View in Reaxys 272/395 Yield

Conditions & References Time= 12h, Ambient temperature Weber, Edwin; Koehler, Hans-Juergen; Reuter, Hans; Journal of Organic Chemistry; vol. 56; nb. 3; (1991); p. 1236 - 1242 View in Reaxys

13C 2

N 13 C

13C

H N N 13 C O

Rx-ID: 5343421 View in Reaxys 273/395 Yield

Conditions & References

78 %, 12 %, 2 %, 4 %

T= 600 °C , Rearrangement

4 % Chromat., 25 % Chromat., 18 % Chromat., 12 % Chromat.

T= 750 °C , Rearrangement, decomposition, Product distribution, Further Variations: Temperatures

Clark, Adrian D.; Ha, Uyen T.; Prager, Rolf H.; Smith, Jason A.; Australian Journal of Chemistry; vol. 52; nb. 11; (1999); p. 1029 - 1033 View in Reaxys

H N

NH 2

Rx-ID: 5818186 View in Reaxys 274/395 Yield

Conditions & References T= 250 - 280 °C , Pyrolysis Davidson; Karten; Journal of the American Chemical Society; vol. 78; (1956); p. 1066 View in Reaxys 2H

Cl N 2H

2H 2H

Rx-ID: 9006823 View in Reaxys 275/395 Yield

Conditions & References Turro, Nicholas J.; Lei, Xue-Gong; Jockusch, Steffen; Li, Wei; Liu, Zhiqiang; Abrams, Lloyd; Ottaviani, M. Francesca; Journal of Organic Chemistry; vol. 67; nb. 8; (2002); p. 2606 - 2618 View in Reaxys

89/122

2016-03-14 02:10:57

H N

Rx-ID: 1585337 View in Reaxys 276/395 Yield

Conditions & References

35 % Chromat., 3 % Chromat., 3 % Chromat., 39 % Chromat.

T= 0 °C , Irradiation, filter: solution of sodium hydrogen phthalate-NaNO2, Further byproducts given

39 % Chromat., 3 % Chromat., 3 % Chromat., 35 % Chromat.

T= 0 °C , Irradiation, filter: solution of sodium hydrogen phthalate-NaNO2, Further byproducts given

Chow, Yuan L.; Polo, Joel S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1986); p. 727 - 734 View in Reaxys

N Z

Z Cl N

Rx-ID: 2102973 View in Reaxys 277/395 Yield

Conditions & References

19 %, 34 % With sulfur in N,N-dimethyl-formamide, Time= 7h, Heating, Product distribution Guillanton, Georges le; Do, Quang Tho; Simonet, Jacques; Bulletin de la Societe Chimique de France; nb. 3; (1989); p. 433 - 440 View in Reaxys

NH O

Rx-ID: 2611474 View in Reaxys 278/395 Yield

Conditions & References in methanol, Time= 0.25h, Heating, Yield given. Yields of byproduct given Jiricny, Josef; Orere, Daniel M.; Reese, Colin B.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1487 - 1492 View in Reaxys O

O N H

N N

H 2N

Rx-ID: 3748014 View in Reaxys 279/395 Yield 45 %, 26 %, 6 %

Conditions & References in 1,2-dichloro-benzene, Heating, Mechanism Belinka, Benjamin A.; Hassner, Alfred; Hendler, J. M.; Journal of Organic Chemistry; vol. 46; nb. 3; (1981); p. 631 - 632

90/122

2016-03-14 02:10:57

View in Reaxys 2H

Rx-ID: 4571531 View in Reaxys 280/395 Yield

Conditions & References Yield given. Multistep reaction Fleming, Ian; Solay, Monica; Stolwijk, Frederik; Journal of Organometallic Chemistry; vol. 521; nb. 1-2; (1996); p. 121 - 124 View in Reaxys

H 2N

tar

Rx-ID: 5746247 View in Reaxys 281/395 Yield

Conditions & References

15 %, 5 %

With ammonia, KNH2, Time= 2.5h, T= -33 °C , Mechanism, Product distribution Streef, J. W.; Hertog, H. J. den; Plas, H. C. van der; Journal of Heterocyclic Chemistry; vol. 22; (1985); p. 985 - 991 View in Reaxys

13C 2

N 13 C

H N O

13C

Rx-ID: 8534763 View in Reaxys 282/395 Yield

Conditions & References

25 % Chromat., 18 % Chromat., 12 % Chromat.

Stage 1:T= 750 °C , Rearrangement Stage 2:Heating, Addition, Further byproducts given Clark, Adrian D.; Ha, Uyen T.; Prager, Rolf H.; Smith, Jason A.; Australian Journal of Chemistry; vol. 52; nb. 11; (1999); p. 1029 - 1033 View in Reaxys

Rx-ID: 8679829 View in Reaxys 283/395 Yield 36 %, 10 %, 6 %

Conditions & References in hexane, Irradiation, Product distribution Jarikov; Neckers; Journal of Organic Chemistry; vol. 66; nb. 3; (2001); p. 659 - 671 View in Reaxys

H C– N

Li+

Rx-ID: 1767498 View in Reaxys 284/395

91/122

2016-03-14 02:10:57

Yield

Conditions & References in tetrahydrofuran, T= 25 °C , Equilibrium constant Antipin, I. S.; Gareev, R. F.; Vedernikov, A. N.; Konovalov, A. I.; Journal of Organic Chemistry USSR (English Translation); vol. 25; nb. 6.1; (1989); p. 1039 - 1044; Zhurnal Organicheskoi Khimii; vol. 25; nb. 6; (1989); p. 1153 1160 View in Reaxys in benzene, T= 24.9 °C , Equilibrium constant Antipin, I. S.; Vedernikov, A. N.; Solomonov, B. N.; Konovalov, A. I.; Journal of Organic Chemistry USSR (English Translation); vol. 25; nb. 101; (1989); p. 1861 - 1865; Zhurnal Organicheskoi Khimii; vol. 25; nb. 10; (1989); p. 2060 2065 View in Reaxys in various solvent(s), T= 24.9 °C , Equilibrium constant Antipin, I. S.; Vedernikov, A. N.; Solomonov, B. N.; Konovalov, A. I.; Journal of Organic Chemistry USSR (English Translation); vol. 25; nb. 101; (1989); p. 1861 - 1865; Zhurnal Organicheskoi Khimii; vol. 25; nb. 10; (1989); p. 2060 2065 View in Reaxys

Li O

H C–

Li+

Rx-ID: 2073088 View in Reaxys 285/395 Yield

H C– N

Li+

Rx-ID: 2409426 View in Reaxys 286/395 Yield

Conditions & References in tetrahydrofuran, T= 25 °C , Equilibrium constant

92/122

2016-03-14 02:10:57

Antipin, I. S.; Gareev, R. F.; Vedernikov, A. N.; Konovalov, A. I.; Journal of Organic Chemistry USSR (English Translation); vol. 25; nb. 6.1; (1989); p. 1039 - 1044; Zhurnal Organicheskoi Khimii; vol. 25; nb. 6; (1989); p. 1153 1160 View in Reaxys in benzene, T= 24.9 °C , Equilibrium constant Antipin, I. S.; Vedernikov, A. N.; Solomonov, B. N.; Konovalov, A. I.; Journal of Organic Chemistry USSR (English Translation); vol. 25; nb. 101; (1989); p. 1861 - 1865; Zhurnal Organicheskoi Khimii; vol. 25; nb. 10; (1989); p. 2060 2065 View in Reaxys in various solvent(s), T= 24.9 °C , Equilibrium constant Antipin, I. S.; Vedernikov, A. N.; Solomonov, B. N.; Konovalov, A. I.; Journal of Organic Chemistry USSR (English Translation); vol. 25; nb. 101; (1989); p. 1861 - 1865; Zhurnal Organicheskoi Khimii; vol. 25; nb. 10; (1989); p. 2060 2065 View in Reaxys

Li O

H C–

O Li+

Rx-ID: 2409428 View in Reaxys 287/395 Yield

O O

N N

HO N

Rx-ID: 3838649 View in Reaxys 288/395 Yield 41 %, 32 %, 4 %

Conditions & References in 1,2-dichloro-benzene, Heating, Mechanism Belinka, Benjamin A.; Hassner, Alfred; Hendler, J. M.; Journal of Organic Chemistry; vol. 46; nb. 3; (1981); p. 631 - 632 View in Reaxys Rx-ID: 8426083 View in Reaxys 289/395

93/122

2016-03-14 02:10:57

Yield

Conditions & References With tetraethylammonium bromide, NOBF4 in benzene, Time= 1h, T= -78 °C , search for ethynyl cation; various solvents and nitosyl agents, Product distribution, Mechanism Alvarez, Roberto Martinez; Hanack, Michael; Schmid, Thomas; Subramanian, L. R.; Journal of Physical Organic Chemistry; vol. 8; (1995); p. 191 - 194 View in Reaxys

NH N

Rx-ID: 9184450 View in Reaxys 290/395 Yield

Conditions & References With HT-1, T= 450 °C , Product distribution, Further Variations: Catalysts, Temperatures Moyano, Elizabeth L.; Del Arco, Margarita; Rives, Vicente; Yranzo, Gloria I.; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8147 - 8150 View in Reaxys

Cl (v4)

Th Cl ClCl

(v4)

Th ClCl

Rx-ID: 26809582 View in Reaxys 291/395 Yield

Conditions & References mixing freshly sublimed ThCl4 with C6H5CH2CN under dry N2 Perrot, R.; Devin, C.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 246; (1958); p. 772 - 774 ; (from Gmelin) View in Reaxys mixing freshly sublimed ThCl4 with C6H5CH2CN under dry N2 vol. Th: SVol.E; 1.2, page 1 - 27 ; (from Gmelin) View in Reaxys

N O

Rx-ID: 320796 View in Reaxys 292/395 Yield

Conditions & References Curtius; Kenngott; Journal fuer Praktische Chemie (Leipzig); vol. <2> 112; (1926); p. 325 View in Reaxys O OH

N N

Rx-ID: 1871452 View in Reaxys 293/395 Yield 33 %, 28 %, 9 %

94/122

2016-03-14 02:10:57

N HO

NH N

Rx-ID: 2059738 View in Reaxys 294/395 Yield

Conditions & References

32 %, 39 %, 9 %, 4 %, 5 %, 3 %

S N

Ohsawa, Akio; Kawaguchi Takayuki; Igeta Hiroshi; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 12; (1982); p. 4352 - 4358 View in Reaxys

O N

T= 800 °C , p= 0.001 - 0.01Torr , approximate contact time: 0.002-0.03 s

Rx-ID: 2186300 View in Reaxys 295/395 Yield

Conditions & References

22.2 %, T= 650 °C , flash vacuum pyrolysis, pyrolysis in solution, various temperatures and solvents, Product distribution, 66.6 %, 6.2 Mechanism % Abramovitch, Rudolph A.; Kress, Albert O.; Pillay, Kutten S.; Thompson, W. Marshall; Journal of Organic Chemistry; vol. 50; nb. 12; (1985); p. 2066 - 2073 View in Reaxys

Cl N

Rx-ID: 2893587 View in Reaxys 296/395 Yield

Conditions & References

0.5 %, 1.9 %

in acetonitrile, Time= 22h, Irradiation Lapin, Stephen; Kurz, Michael E.; Journal of the Chemical Society, Chemical Communications; nb. 16; (1981); p. 817 - 818 View in Reaxys

1.9 %, 0.5 %

in acetonitrile, Irradiation, different times of photolysis; different concentration ratios, Product distribution, Mechanism Kurz, M. E.; Lapin, S. C.; Miriam, K.; Hagen, T. J.; Qian, X. Q.; Journal of Organic Chemistry; vol. 49; (1984); p. 2728 - 2733 View in Reaxys 2H

N–

C– N

Li+

Rx-ID: 3180135 View in Reaxys 297/395 Yield

Conditions & References Zarges, Wolfgang; Marsch, Michael; Harms, Klaus; Boche, Gernot; Angewandte Chemie; vol. 101; nb. 10; (1989); p. 1424 - 1425 View in Reaxys

95/122

2016-03-14 02:10:57

Rx-ID: 3566570 View in Reaxys 298/395 Yield

Conditions & References

21 % Spectr.

Time= 1h, T= 400 °C , p= 0.01Torr , Product distribution, Mechanism Hoffmann, Reinhard W.; Barth, Wolfgang; Schuettler, Reinhard; Mayer, Bernhard; Chemische Berichte; vol. 119; nb. 11; (1986); p. 3297 - 3315 View in Reaxys

Rx-ID: 4266867 View in Reaxys 299/395 Yield

Conditions & References With methanol, T= 25 °C , Equilibrium constant Atherton, John H.; Crampton, Michael R.; Duffield, Gaynor L.; Stevens, J. Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 3; (1995); p. 443 - 448 View in Reaxys

Cl 2Cl SnCl Cl Cl (v2)

N 2 O+

– Cl(v2)

(v2)

Cl N Sn Cl ClCl

Rx-ID: 26594336 View in Reaxys 300/395 Yield

Conditions & References at low temp. Devin, C.; Bulletin de la Societe Chimique de France; (1959); p. 563 - 564 ; (from Gmelin) View in Reaxys at low temp. vol. Sn: MVol.C3; 23.5.9.2, page 107 - 109 ; (from Gmelin) View in Reaxys

O O

Rx-ID: 37302653 View in Reaxys 301/395 Yield

Conditions & References Reaction Steps: 2 1: 600 °C / 0 - 0 Torr 2: 850 °C / 0 - 0 Torr Begue, Didier; Dargelos, Alain; Berstermann, Hans M.; Netsch, Klaus P.; Bednarek, Pawel; Wentrup, Curt; Journal of Organic Chemistry; vol. 79; nb. 3; (2014); p. 1247 - 1253 View in Reaxys Reaction Steps: 2 1: 700 °C / 0 - 0 Torr 2: 850 °C / 0 - 0 Torr Begue, Didier; Dargelos, Alain; Berstermann, Hans M.; Netsch, Klaus P.; Bednarek, Pawel; Wentrup, Curt; Journal of Organic Chemistry; vol. 79; nb. 3; (2014); p. 1247 - 1253

96/122

2016-03-14 02:10:57

View in Reaxys

O O

Rx-ID: 37302656 View in Reaxys 302/395 Yield

Conditions & References Reaction Steps: 3 1: 600 °C / 0 - 0 Torr 2: 700 °C / 0 - 0 Torr 3: 800 °C / 0 - 0 Torr Begue, Didier; Dargelos, Alain; Berstermann, Hans M.; Netsch, Klaus P.; Bednarek, Pawel; Wentrup, Curt; Journal of Organic Chemistry; vol. 79; nb. 3; (2014); p. 1247 - 1253 View in Reaxys Reaction Steps: 3 1: 700 °C / 0 - 0 Torr 2: 700 °C / 0 - 0 Torr 3: 800 °C / 0 - 0 Torr Begue, Didier; Dargelos, Alain; Berstermann, Hans M.; Netsch, Klaus P.; Bednarek, Pawel; Wentrup, Curt; Journal of Organic Chemistry; vol. 79; nb. 3; (2014); p. 1247 - 1253 View in Reaxys

H C–

N O

N O Li+ Li O

N O

Rx-ID: 2093302 View in Reaxys 303/395 Yield

Conditions & References in benzene, T= 24.9 °C , Equilibrium constant Antipin, I. S.; Vedernikov, A. N.; Solomonov, B. N.; Konovalov, A. I.; Journal of Organic Chemistry USSR (English Translation); vol. 25; nb. 101; (1989); p. 1861 - 1865; Zhurnal Organicheskoi Khimii; vol. 25; nb. 10; (1989); p. 2060 2065 View in Reaxys in various solvent(s), T= 24.9 °C , Equilibrium constant Antipin, I. S.; Vedernikov, A. N.; Solomonov, B. N.; Konovalov, A. I.; Journal of Organic Chemistry USSR (English Translation); vol. 25; nb. 101; (1989); p. 1861 - 1865; Zhurnal Organicheskoi Khimii; vol. 25; nb. 10; (1989); p. 2060 2065 View in Reaxys

97/122

2016-03-14 02:10:57

Li O

N O

H C–

N N

N O Li+

Rx-ID: 2409429 View in Reaxys 304/395 Yield

O N

H N

Rx-ID: 5338691 View in Reaxys 305/395 Yield

Conditions & References

54 %, 18 %, 14 %, 11 %

T= 600 °C , Rearrangement, decomposition, Product distribution, Further Variations: Temperatures Clark, Adrian D.; Ha, Uyen T.; Prager, Rolf H.; Smith, Jason A.; Australian Journal of Chemistry; vol. 52; nb. 11; (1999); p. 1029 - 1033 View in Reaxys

N HO

N O

aqueous alkaline solution

Rx-ID: 8236583 View in Reaxys 306/395 Yield

Conditions & References Skinner; Journal of the American Chemical Society; vol. 55; (1933); p. 2036,2037, 2039 View in Reaxys

O O

E N

Rx-ID: 516889 View in Reaxys 307/395

98/122

2016-03-14 02:10:57

Yield

Conditions & References Erhitzen auf Temperaturen oberhalb des Schmelzpunktes und Behandeln des in Aether geloesten Reaktionsprodukts mit wss. Natriumcarbonat-Loesung Barnes; Journal of the American Chemical Society; vol. 57; (1935); p. 937,938 View in Reaxys

(v1)

Rx-ID: 716943 View in Reaxys 308/395 Yield

Conditions & References Schneidewind; Chemische Berichte; vol. 21; (1888); p. 1325 View in Reaxys

O N

H C–

Li+

Rx-ID: 2173444 View in Reaxys 309/395 Yield

H C– N

Li+

Rx-ID: 2409427 View in Reaxys 310/395 Yield

H O

Rx-ID: 5818177 View in Reaxys 311/395 Yield

Conditions & References Gomberg; Buchler; Journal of the American Chemical Society; vol. 42; (1920); p. 2067 View in Reaxys H C–

OH HO

S OO

Na +

Rx-ID: 8259194 View in Reaxys 312/395

99/122

2016-03-14 02:10:57

Yield

Conditions & References Rising; Braun; Journal of the American Chemical Society; vol. 52; (1930); p. 1070,1072 View in Reaxys

N S

O O

O–

O OH HO OH

Rx-ID: 3670460 View in Reaxys 313/395 Yield

Conditions & References T= 200 °C , various temperatures investigated, Product distribution Macleod, Alexander J.; Panesar, Satwinder S.; Gil, Victor; Phytochemistry (Elsevier); vol. 20; nb. 4; (1981); p. 977 - 980 View in Reaxys

NH N

Rx-ID: 4857824 View in Reaxys 314/395 Yield

Conditions & References With 1,1,1-trifluoroethane, T= 776.9 - 1361.9 °C , Arrhenius parameters, Product distribution, Rate constant, Mechanism Laskin; Lifshitz; Journal of Physical Chemistry A; vol. 101; nb. 42; (1997); p. 7787 - 7801 View in Reaxys

N (v2)

Rx-ID: 37087961 View in Reaxys 315/395 Yield

Conditions & References Photolysis Hoj, Martin; Kvaskoff, David; Wentrup, Curt; Journal of Organic Chemistry; vol. 79; nb. 1; (2014); p. 307 - 313 View in Reaxys

H N

N H O

Rx-ID: 262567 View in Reaxys 316/395 Yield

Conditions & References T= 300 °C Stolle; Stevens; Journal fuer Praktische Chemie (Leipzig); vol. <2> 69; (1904); p. 378 View in Reaxys T= 300 °C Stolle; Stevens; Journal fuer Praktische Chemie (Leipzig); vol. <2> 69; (1904); p. 378 View in Reaxys

100/122

2016-03-14 02:10:57

O O Z N

N O N

N O

Rx-ID: 2036705 View in Reaxys 317/395 Yield

Conditions & References

34 % Chromat., 11 % Chromat., 6 % Chromat., 6 % Chromat., 2 % Chromat., 27 % Chromat.

T= 900 °C , p= 0.03Torr , further iminoisobenzofuran-1-ones, Product distribution Brown, Roger F. C.; Coulston, Karen J.; Eastwood, Frank W.; Australian Journal of Chemistry; vol. 47; nb. 1; (1994); p. 47 - 60 View in Reaxys

OH O E N

OH S

S O–

O HO

Rx-ID: 3670211 View in Reaxys 318/395 Yield

Conditions & References With Fe(NO3)*9H2O, Time= 0.25h, Ambient temperature, Lepidium sativum seed autolysate, various concentration of Fe(3+), Fe(2+), Cu(1+) salts, Product distribution Hasapis, Xenophon; MacLeod, Alexander J.; Phytochemistry (Elsevier); vol. 21; nb. 3; (1982); p. 559 - 564 View in Reaxys

N H

–

Rx-ID: 5818185 View in Reaxys 319/395 Yield

Conditions & References Bergstrom; Agostinho; Journal of the American Chemical Society; vol. 67; (1945); p. 2153 View in Reaxys

N H

Rx-ID: 5818178 View in Reaxys 320/395 Yield

Conditions & References T= 450 - 460 °C , beim Leiten ueber ThO2, sowie bei 480-490grad Mailhe; Annales de Chimie (Cachan, France); vol. <9>13; (1920); p. 210; ; vol. 15; p. 9550; Chem. Zentralbl.; vol. 91; nb. I; (1920); p. 115 View in Reaxys

101/122

2016-03-14 02:10:57

Mailhe; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 166; (1918); p. 36; Annales de Chimie (Cachan, France); vol. <9> 13; (1920); p. 218 View in Reaxys S N H

N H

iron

paraffin oil

Rx-ID: 6680288 View in Reaxys 321/395 Yield

Conditions & References T= 280 °C Patent; Bayer and Co.; DE259363; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 204 View in Reaxys

Rx-ID: 750271 View in Reaxys 322/395 Yield

Conditions & References T= 670 °C , Dampfphasen-Reaktion Patent; Am. Cyanamid Co.; US2553404; (1950) View in Reaxys N

Rx-ID: 750272 View in Reaxys 323/395 Yield

Conditions & References T= 670 °C Patent; Am. Cyanamid Co.; US2553404; (1950) View in Reaxys Patent; Am. Cyanamid Co.; DE848358; (1951); View in Reaxys

(v2)

N N

HN N

N N

Rx-ID: 1985749 View in Reaxys 324/395

102/122

2016-03-14 02:10:57

Yield

Conditions & References

25 %, 21 T= 25 °C , Rate constant, Mechanism %, 50 %, 10 %, 18 % Tomilenko, E. I.; Staninets, V. I.; Kukhar', V. P.; Beletskaya, I. P.; Doklady Chemistry; vol. 252; (1980); p. 224 - 226; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 252; nb. 1; (1980); p. 129 - 132 View in Reaxys

Rx-ID: 3536895 View in Reaxys 325/395 Yield

Conditions & References

26 % Chro- plasma apparatus; a variety of substituted benzenes and pyridine similarly cyanated, Product distribution mat., 21 % Chromat., So, Ying-Hung; Miller, Larry L.; Journal of the American Chemical Society; vol. 102; nb. 23; (1980); p. 7119 - 7120 13 % Chro- View in Reaxys mat., 11 % Chromat., 5 % Chromat.

CuCl

Rx-ID: 5818180 View in Reaxys 326/395 Yield

Conditions & References T= 80 - 100 °C Kurtz in K. Ziegler; View in Reaxys

H N

nickel

H 2N

Rx-ID: 5818182 View in Reaxys 327/395 Yield

Conditions & References T= 225 °C Mignonac; Annales de Chimie (Cachan, France); vol. <11> 2; (1934); p. 225,242 View in Reaxys

OH H

silica gel

H 2N

Rx-ID: 5818183 View in Reaxys 328/395 Yield

Conditions & References T= 430 - 450 °C Patent; I.G. Farbenind.; DE482943; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 699 View in Reaxys

103/122

2016-03-14 02:10:57

N O

HO O

Rx-ID: 7441929 View in Reaxys 329/395 Yield

Conditions & References T= 150 - 160 °C Hessler; American Chemical Journal; vol. 32; (1904); p. 120 View in Reaxys

copper

N OH

N O

NH 2

Rx-ID: 7450167 View in Reaxys 330/395 Yield

Conditions & References T= 200 °C Yamaguchi; Bulletin of the Chemical Society of Japan; vol. 1; (1926); p. 38; Memoirs of the College of Science, Kyoto Imperial University; vol. <A> 9; (1926); p. 431; Chem. Zentralbl.; vol. 97; nb. I; (1926); p. 3538 View in Reaxys

NH 2

H 2N

tar

N Br

NH 2

Rx-ID: 8428073 View in Reaxys 331/395 Yield

Conditions & References

10 %, 10 With ammonia, KNH2, Time= 0.0333333h, Mechanism, Product distribution %, 10 %, 5 Streef, J. W.; Hertog, H. J. den; Plas, H. C. van der; Journal of Heterocyclic Chemistry; vol. 22; (1985); p. 985 - 991 % View in Reaxys N

Rx-ID: 328925 View in Reaxys 332/395 Yield

Conditions & References T= 320 °C Henze; Chemische Berichte; vol. 31; (1898); p. 3065 View in Reaxys

N+ N

Cl –

Rx-ID: 589149 View in Reaxys 333/395 Yield

Conditions & References T= 130 - 230 °C

104/122

2016-03-14 02:10:57

v. Meyer,E.; Chem. Zentralbl.; vol. 80; nb. II; (1909); p. 1801 View in Reaxys

13C 2 13

N 13 C

13C

13CH

Rx-ID: 5342656 View in Reaxys 334/395 Yield

Conditions & References

27 % Chromat., 12 % Chromat., 8 % Chromat.

T= 750 °C , Rearrangement, decomposition, Product distribution Clark, Adrian D.; Ha, Uyen T.; Prager, Rolf H.; Smith, Jason A.; Australian Journal of Chemistry; vol. 52; nb. 11; (1999); p. 1029 - 1033 View in Reaxys

N O

H O

Rx-ID: 7441930 View in Reaxys 335/395 Yield

Conditions & References T= 100 °C Volhard; Henke; Justus Liebigs Annalen der Chemie; vol. 282; (1894); p. 66,81 View in Reaxys

N O

diluted alcoholic ammonia O N

O HN

Rx-ID: 7441931 View in Reaxys 336/395 Yield

Conditions & References T= 100 °C Volhard; Henke; Justus Liebigs Annalen der Chemie; vol. 282; (1894); p. 66,81 View in Reaxys

H N

O HO

palladium

Rx-ID: 8260144 View in Reaxys 337/395 Yield

Conditions & References T= 20 °C Kindler; Schrader; Justus Liebigs Annalen der Chemie; vol. 564; (1949); p. 49,51, 52 View in Reaxys

105/122

2016-03-14 02:10:57

N H

H 2N

NH 2

Rx-ID: 5818184 View in Reaxys 338/395 Yield

Conditions & References T= 180 °C Davies; Piggott; Journal of the Chemical Society; (1945); p. 347 Anm. View in Reaxys

H 2N

NH 2

(+-)-3-imino-2-phenyl-propionic acid nitrile

N N N

Rx-ID: 7054876 View in Reaxys 339/395 Yield

Conditions & References T= 180 °C Davies; Piggott; Journal of the Chemical Society; (1945); p. 347 Anm. View in Reaxys

H 2N

NH 2

N N

H 2N

Rx-ID: 7916187 View in Reaxys 340/395 Yield

Conditions & References T= 180 °C Davies; Piggott; Journal of the Chemical Society; (1945); p. 347 Anm. View in Reaxys

N H N

H N

H 2N

NH 2

N N N

Rx-ID: 7916188 View in Reaxys 341/395 Yield

Conditions & References T= 180 °C Davies; Piggott; Journal of the Chemical Society; (1945); p. 347 Anm. View in Reaxys

NH 2

Rx-ID: 378928 View in Reaxys 342/395 Yield

Conditions & References bei der Destillation im Vakuum

106/122

2016-03-14 02:10:57

Bary; Bulletin des Societes Chimiques Belges; vol. 31; (1922); p. 408; Chem. Zentralbl.; vol. 94; nb. III; (1923); p. 124 View in Reaxys Rondou; Bulletin des Societes Chimiques Belges; vol. 31; (1922); p. 237,238; Chem. Zentralbl.; vol. 94; nb. I; (1923); p. 88 View in Reaxys

O HO

aqueous alkaline solution

OH O

Rx-ID: 8236582 View in Reaxys 343/395 Yield

Conditions & References optically inactive isomer of mp: 200 degree Cordier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 200; (1935); p. 1412 View in Reaxys optically inactive isomer of mp: 158 degree Cordier; Moreau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 217; (1943); p. 199 View in Reaxys

O N

E N

H O

NH 2

Rx-ID: 8255575 View in Reaxys 344/395 Yield

Conditions & References T= 100 °C Volhard; Henke; Justus Liebigs Annalen der Chemie; vol. 282; (1894); p. 66,81 View in Reaxys

O HO

Rx-ID: 459891 View in Reaxys 345/395 Yield

Conditions & References bei der Wasserdampf-Destillation Levy; Wellisch; Bulletin de la Societe Chimique de France; vol. <4> 45; (1929); p. 940 View in Reaxys

O N

OH O

107/122

2016-03-14 02:10:57

H N

N O

Rx-ID: 1585335 View in Reaxys 346/395 Yield

Conditions & References

3 % Chromat., 3 % Chromat., 2 % Chromat., 35 % Chromat., 39 % Chromat.

T= 0 °C , Irradiation, filter: solution of sodium hydrogen phthalate-sodium nitrite, irradiation of N-nitrozo-N-acetyl-αamino-acids between var. conditions, Product distribution, Mechanism Chow, Yuan L.; Polo, Joel S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1986); p. 727 - 734 View in Reaxys

aq. barium hydroxide solution

Rx-ID: 8236575 View in Reaxys 347/395 Yield

Conditions & References Destillieren des Reaktionsprodukts mit Wasserdampf Rinkes; Recueil des Travaux Chimiques des Pays-Bas; vol. 39; (1920); p. 707 View in Reaxys

Rx-ID: 288131 View in Reaxys 348/395 Yield

Conditions & References Bernthsen; Justus Liebigs Annalen der Chemie; vol. 192; (1878); p. 5,19; Justus Liebigs Annalen der Chemie; vol. 224; (1884); p. 1 View in Reaxys

S SH

Rx-ID: 456484 View in Reaxys 349/395 Yield

Conditions & References Bernthsen; Justus Liebigs Annalen der Chemie; vol. 192; (1878); p. 5,19; Justus Liebigs Annalen der Chemie; vol. 224; (1884); p. 1 View in Reaxys

O S N

H O

O–

K+

Rx-ID: 544639 View in Reaxys 350/395 Yield

Conditions & References Barbaglia; Chemische Berichte; vol. 5; (1872); p. 271 View in Reaxys

108/122

2016-03-14 02:10:57

Rx-ID: 558691 View in Reaxys 351/395 Yield

Conditions & References Dollfus; Chemische Berichte; vol. 25; (1892); p. 1918; Chemische Berichte; vol. 26; (1893); p. 1971 View in Reaxys

O OH

Rx-ID: 731487 View in Reaxys 352/395 Yield

Conditions & References bei der Destillation Luckenbach; Chemische Berichte; vol. 17; (1884); p. 1423 View in Reaxys

Rx-ID: 3536833 View in Reaxys 353/395 Yield

Conditions & References calculated (BEBO and equibonding method) activation energies for hydrogen atom transfer reaction, anodic cyanation, Thermodynamic data, Mechanism Eberson, Lennart; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 34; nb. 7; (1980); p. 481 - 492 View in Reaxys

N O

alkali

N O

Rx-ID: 5818187 View in Reaxys 354/395 Yield

Conditions & References Erlenmeyer junior; Justus Liebigs Annalen der Chemie; vol. 271; (1892); p. 174 View in Reaxys

S H

NH 2

H S

Rx-ID: 6680289 View in Reaxys 355/395 Yield

Conditions & References bei der Destillation Bernthsen; Justus Liebigs Annalen der Chemie; vol. 184; (1877); p. 300 View in Reaxys

S NH 2

KOH-solution

H S

Rx-ID: 6680293 View in Reaxys 356/395

109/122

2016-03-14 02:10:57

Yield

Conditions & References Bernthsen; Justus Liebigs Annalen der Chemie; vol. 184; (1877); p. 300 View in Reaxys

sodium hypochlorite

H 2N

Rx-ID: 7054874 View in Reaxys 357/395 Yield

Conditions & References Rinkes; Recueil des Travaux Chimiques des Pays-Bas; vol. 39; (1920); p. 707 View in Reaxys

O HO

natrium carbonate

N OH

dibenzylfuroxane

Rx-ID: 7922607 View in Reaxys 358/395 Yield

Conditions & References Bougault; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 165; (1917); p. 592; Bulletin de la Societe Chimique de France; vol. <4> 25; (1919); p. 385 View in Reaxys

N O HO

palladium

Rx-ID: 8236576 View in Reaxys 359/395 Yield

Conditions & References Hydrogenation Kindler; Schrader; Justus Liebigs Annalen der Chemie; vol. 564; (1949); p. 49,51, 52 View in Reaxys

N O O

palladium

Rx-ID: 8236577 View in Reaxys 360/395 Yield

Conditions & References Hydrogenation Kindler; Schrader; Justus Liebigs Annalen der Chemie; vol. 564; (1949); p. 49,51, 52 View in Reaxys

H 2N O

natrium carbonate

Rx-ID: 8236578 View in Reaxys 361/395 Yield

Conditions & References Volhard; Henke; Justus Liebigs Annalen der Chemie; vol. 282; (1894); p. 66,81

110/122

2016-03-14 02:10:57

View in Reaxys

N O

aqueous alkaline solution

Rx-ID: 8236579 View in Reaxys 362/395 Yield

Conditions & References Schreiber; Annales de Chimie (Cachan, France); vol. <12> 2; (1947); p. 84,120 View in Reaxys

N O

alkali

OH O

O N

Rx-ID: 8236580 View in Reaxys 363/395 Yield

Conditions & References Bodronx; Bulletin de la Societe Chimique de France; vol. <4> 9; (1911); p. 655 View in Reaxys N HO

aqueous alkaline solution

Rx-ID: 8255180 View in Reaxys 364/395 Yield

Conditions & References Schreiber; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 217; (1943); p. 353,354; Annales de Chimie (Cachan, France); vol. <12> 2; (1947); p. 84,106 View in Reaxys

O OH

concentrated aqueous alkaline solution

HO O

Rx-ID: 8258735 View in Reaxys 365/395 Yield

Conditions & References Cordier; Moreau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 214; (1942); p. 621 View in Reaxys

N O

aqueous alkaline solution

OH O

Rx-ID: 8259274 View in Reaxys 366/395 Yield

Conditions & References Schreiber; Annales de Chimie (Cachan, France); vol. <12> 2; (1947); p. 84,120 View in Reaxys

111/122

2016-03-14 02:10:57

O–

F F F

S O

S+

S S

Rx-ID: 3738404 View in Reaxys 367/395 Yield

Conditions & References Ambient temperature, Irradiation, var. solvents and sensitizers, Product distribution, Mechanism, Quantum yield Dektar, John L.; Hacker, Nigel P.; Journal of Organic Chemistry; vol. 53; nb. 8; (1988); p. 1833 - 1835 View in Reaxys

copper (I)-cyanide

Rx-ID: 5818179 View in Reaxys 368/395 Yield

Conditions & References ultraviolettes Licht Rosenmund; Luxat; Tiedemann; Chemische Berichte; vol. 56; (1923); p. 1955 View in Reaxys

S OH

HgCl2

NH 2

Rx-ID: 6680291 View in Reaxys 369/395 Yield

Conditions & References Bernthsen; Justus Liebigs Annalen der Chemie; vol. 184; (1877); p. 300 View in Reaxys

S OH

HgO

NH 2

Rx-ID: 6680292 View in Reaxys 370/395 Yield

Conditions & References Bernthsen; Justus Liebigs Annalen der Chemie; vol. 184; (1877); p. 300 View in Reaxys

H N H

alkali

N H

Rx-ID: 7054875 View in Reaxys 371/395 Yield

Conditions & References Walther; Schickler; Journal fuer Praktische Chemie (Leipzig); vol. <2> 55; (1897); p. 323 View in Reaxys

112/122

2016-03-14 02:10:57

OH OH

H 2N

NH 2

Rx-ID: 7441928 View in Reaxys 372/395 Yield

Conditions & References Purgotti; Gazzetta Chimica Italiana; vol. 25 I; (1895); p. 120 View in Reaxys N HO

alkali

N O

O O

Rx-ID: 7918017 View in Reaxys 373/395 Yield

Conditions & References Bodroux; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 151; (1910); p. 235; Bulletin de la Societe Chimique de France; vol. <4> 7; (1910); p. 847,850 View in Reaxys

N O– Na +

'kyanbenzyline'

N NH 2

Rx-ID: 8236581 View in Reaxys 374/395 Yield

Conditions & References Ingold; Journal of the Chemical Society; vol. 125; (1924); p. 1322 View in Reaxys

N O HN

H 2N

O H N

H N

N H

H N

phenylcyanopyruvic acid ethyl ester-phenyl‐ hydrazone of mp: 107-108 degree

N H O

Rx-ID: 6218352 View in Reaxys 375/395 Yield

Conditions & References Erlenmeyer; Chemische Berichte; vol. 33; p. 2592 View in Reaxys

–O

O Pb4+

NH 2

H S

Rx-ID: 6680290 View in Reaxys 376/395 Yield

Conditions & References Bernthsen; Justus Liebigs Annalen der Chemie; vol. 184; (1877); p. 300 View in Reaxys

113/122

2016-03-14 02:10:57

N H

palladium black H

N N

Rx-ID: 7916189 View in Reaxys 377/395 Yield

Conditions & References Knoevenagel; Bergdolt; Chemische Berichte; vol. 36; (1903); p. 2861 View in Reaxys

N O HO

palladium

H N

O N

Rx-ID: 7919415 View in Reaxys 378/395 Yield

Conditions & References Kindler; Peschke; Justus Liebigs Annalen der Chemie; vol. 564; (1949); p. 49,53 View in Reaxys

O HO

S O

Rx-ID: 24470509 View in Reaxys 379/395 Yield 76%

Conditions & References viii : (viii) (viii) Trimethylammonium phenyl acetonitrile p-dodecyl benzene sulphonate This material was prepared, using a method analogous to that in (vi), vide supra, except that dimethylamino phenyl acetonitrile was used instead of dimethylamino propionitrile. A white solid (7.66 g, yield 76percent) was obtained. 'H NMR assay (CDCl3, trioxan) 99percent (σ, CDCl3) 0.7-1.7 (complex unresolved, 24H, C12 H25), STR13 3.55 (s, 9H, (CH3)3 N+), 6.85 (s, IH, N--CH), 7.15 (d, 2H, ArH, 7.5 (d, 2H, ArH) 7.6 (d, IH, ArH), 7.8 (2d, 4H, ArH) ppm. Patent; Lever Brothers Company, Division of Conopco, Inc.; US5281361; (1994); (A1) English View in Reaxys

Rx-ID: 24904516 View in Reaxys 380/395

114/122

2016-03-14 02:10:57

Yield

Conditions & References

82.0%

5 : Alkylation of Benzyl Cyanide Example 5 Alkylation of Benzyl Cyanide Hexadecyltributyl phosphonium hectorite (0.050 mmol) was mixed with 2.0 ml of 50 wt percent of aqueous sodium hydroxide, 1-bromopentane (5.0 mmol) and benzyl cyanide 95.0 mmol). After reaction at 50° C. for 2 hr, the emulsion was broken by centrifugation and 1-cyano-1-phenyl hexane was obtained in 82.0percent yield. Patent; Michigan State University; US5099054; (1992); (A1) English View in Reaxys

Rx-ID: 5589574 View in Reaxys 381/395 Yield

Conditions & References Herstellung von Phenyl-<1-14 C>acetonitril Vaughan; McCane; Journal of the American Chemical Society; vol. 76; (1954); p. 2504 View in Reaxys Block; Zeitschrift fuer Naturforschung; vol. 8b; (1953); p. 440,443 View in Reaxys Brown,R.F.C. et al.; Australian Journal of Chemistry; vol. 26; (1973); p. 1319 - 1326 View in Reaxys Ahmad,A.; Spenser,I.D.; Canadian Journal of Chemistry; vol. 39; (1961); p. 1340 - 1359 View in Reaxys Kindler,K.; Luehrs,K.; Chemische Berichte; vol. 99; (1966); p. 227 - 232 View in Reaxys Hooz,J.; Linke,S.; Journal of the American Chemical Society; vol. 90; (1968); p. 6891 - 6892 View in Reaxys Tanner,D.D.; Bunce,N.J.; Journal of the American Chemical Society; vol. 91; (1969); p. 3028 - 3034 View in Reaxys Kobler,H. et al.; Justus Liebigs Annalen der Chemie; (1978); p. 1946 - 1962 View in Reaxys Caubere,P.; Loubinoux,B.; Bulletin de la Societe Chimique de France; (1968); p. 3857 - 3861 View in Reaxys Ogata,M.; Matsumoto,H.; Heterocycles; vol. 11; (1978); p. 139 - 147 View in Reaxys Kalvoda,J.; Kaufmann,H.; Journal of the Chemical Society, Chemical Communications; (1976); p. 209 - 210 View in Reaxys Ferris,A.F.; Journal of Organic Chemistry; vol. 25; (1960); p. 12 - 18 View in Reaxys Smolinsky,G.; Feuer,B.I.; Journal of Organic Chemistry; vol. 31; (1966); p. 3882 - 3884 View in Reaxys Fedotov,N.S. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 42; nb. 2; (1972); p. 358 - 363,348 - 353 View in Reaxys Sakota; Koine; Okita; Nippon Kagaku Zasshi; vol. 90; (1969); p. 77,78; ; vol. 70; (1969); p. 115517 View in Reaxys Ellzey et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 846 View in Reaxys Kanaoka et al.; Chemical and Pharmaceutical Bulletin; vol. 18; (1970); p. 397,398 View in Reaxys Campagna et al.; Tetrahedron Letters; (1977); p. 1813 View in Reaxys Patent; Rhone-Poulenc S/A; DE2205360; (1972); ; vol. 77; nb. 151710 View in Reaxys Luecke; Winter; Chimia; vol. 25; (1971); p. 94 View in Reaxys Patent; Rhone-Poulenc; US3884957; (1975); ; vol. 83; nb. 58487

115/122

2016-03-14 02:10:57

View in Reaxys Patent; Schering AG; DE2909871; (1979); ; vol. 93; nb. 239193 View in Reaxys Rossi et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 3371 View in Reaxys Ahmad; Synthesis; (1976); p. 418 View in Reaxys Selvarajan; Boyer; Journal of Heterocyclic Chemistry; vol. 9; (1972); p. 87 View in Reaxys Boyer; Frints; Journal of Heterocyclic Chemistry; vol. 7; (1970); p. 71 View in Reaxys Gillis; Dain; Journal of Organic Chemistry; vol. 36; (1971); p. 518 View in Reaxys Schmitz; Janisch; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 10; (1974); p. 1432,1436; Khimiya Geterotsiklicheskikh Soedinenii; vol. 10; (1974); p. 1629 View in Reaxys Patent; Dt. Akad. Wiss.; DE1443704; (1969); ; vol. 72; nb. 54358; (1970) View in Reaxys Mikol; Boyer; Journal of the Chemical Society, Chemical Communications; nb. 8; (1972); p. 439 - 439 View in Reaxys Shvartsberg et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 25; (1976); p. 2138; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 25; (1976); p. 2292 View in Reaxys Trippett; Walker; Journal of the Chemical Society; (1960); p. 2976 View in Reaxys Saraie et al.; Tetrahedron Letters; (1973); p. 2121,2123 View in Reaxys Forestiere; Sillion; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 284; (1977); p. 897 View in Reaxys Brown et al.; Journal of the American Chemical Society; vol. 91; (1969); p. 6852 View in Reaxys Gross; Gloede; Chemische Berichte; vol. 96; (1963); p. 1387,1391 View in Reaxys Eilingsfeld et al.; Angewandte Chemie; vol. 72; (1960); p. 836,837 View in Reaxys Suzuki et al.; Synthesis; (1978); p. 905 View in Reaxys Avril et al.; Journal of Chemical Research, Miniprint; (1979); p. 2921,2924,2932 View in Reaxys Lohaus; Chemische Berichte; vol. 100; nb. 8; (1967); p. 2719 View in Reaxys Caubere; Bulletin de la Societe Chimique de France; (1967); p. 3446 View in Reaxys Boyer et al.; Journal of Organic Chemistry; vol. 34; nb. 6; (1969); p. 1987 View in Reaxys Boyer; Selvarajan; Tetrahedron Letters; (1969); p. 47 View in Reaxys Semmelhack et al.; Journal of the American Chemical Society; vol. 97; (1975); p. 1247 View in Reaxys Kwiatek; Seyler; Journal of Organometallic Chemistry; vol. 3; (1965); p. 421,429 View in Reaxys Friedman; Shechter; Journal of Organic Chemistry; vol. 25; (1960); p. 877,878 View in Reaxys Sheppard; Journal of Organic Chemistry; vol. 27; (1962); p. 3756,3759 View in Reaxys Sugimoto et al.; Chemical and Pharmaceutical Bulletin; vol. 10; (1962); p. 427 View in Reaxys Gordon et al.; Journal of Organic Chemistry; vol. 28; (1963); p. 698 View in Reaxys Eastham; Cannon; Journal of Organic Chemistry; vol. 25; (1960); p. 1504

116/122

2016-03-14 02:10:57

View in Reaxys Glass et al.; Journal of the Chemical Society [Section] D: Chemical Communications; (1971); p. 1546 View in Reaxys Cook et al.; Journal of Organic Chemistry; vol. 39; (1974); p. 3416 View in Reaxys Schoellkopf; Schroeder; Angewandte Chemie; vol. 85; (1973); p. 402 View in Reaxys Suzuki et al.; Nippon Kagaku Kaishi; (1979); p. 91,92; ; nb. 56711; (1979) View in Reaxys Yanagida et al.; Journal of Organic Chemistry; vol. 44; (1979); p. 1099,1100 View in Reaxys Patent; Deutsche Akademie d. Wissenschaften zu Berlin; GB1005647; (1963); ; vol. 64; nb. 1954h; (1966) View in Reaxys Harrison et al.; Synthesis; (1977); p. 41 View in Reaxys Pereira et al.; Biochimica et Biophysica Acta; vol. 313; (1973); p. 170,172,178 View in Reaxys Olah et al.; Synthesis; (1979); p. 227 View in Reaxys Makosza et al.; Przemysl Chemiczny; vol. 57; (1978); p. 299,301; ; vol. 89; nb. 108568; (1978) View in Reaxys Fukunaga et al.; Nippon Kagaku Kaishi; (1977); p. 1379,1381; ; nb. 5818; (1978) View in Reaxys Saarivirta; Planta Medica; vol. 24; (1973); p. 112,117 View in Reaxys Castro; Selve; Bulletin de la Societe Chimique de France; (1971); p. 2296 View in Reaxys Patent; DU PONT DE NEMOURS and CO.; US3940402; (1976); ; vol. 85; nb. 6388 View in Reaxys Fukunaga; Yuki Gosei Kagaku Kyokaishi; vol. 33; (1975); p. 774 View in Reaxys Kaiser et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 3640,3643 View in Reaxys Monson; Priest; Canadian Journal of Chemistry; vol. 49; (1971); p. 2897 View in Reaxys Furukawa et al.; Chemistry Letters; (1977); p. 1359 View in Reaxys Beijer et al.; Angewandte Chemie; vol. 84; (1972); p. 957 View in Reaxys Graham; Marr; Canadian Journal of Chemistry; vol. 50; (1972); p. 3857 View in Reaxys Lehmkuhl et al.; Synthesis; (1977); p. 184 View in Reaxys Burdon et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1972); p. 639 View in Reaxys Arpe; Leupold; Angewandte Chemie; vol. 84; (1972); p. 767 View in Reaxys Hartke; Angewandte Chemie; vol. 74; (1962); p. 214 View in Reaxys Jonczyk et al.; Angewandte Chemie; vol. 90; (1978); p. 58 View in Reaxys Popow; Schuikin; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); (1960); p. 1349; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1960); p. 1451 View in Reaxys Singh; Gandhi; Synthetic Communications; vol. 9; (1979); p. 569 View in Reaxys Convert; Armand; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 265; (1967); p. 1486 View in Reaxys Isomura et al.; Tetrahedron Letters; (1968); p. 3499

117/122

2016-03-14 02:10:57

View in Reaxys Especially useful activated methylene compounds due to their ready availability and the fact that highly useful vinylcyclopropane derivatives are obtained therefrom are: lower alkyl malonates, such as dimethyl malonate, diethyl malonate, dibutyl malonate and diisopropyl malonate; ... 2,4-pentanedione; phenylacetone; malonamide; malonitrile; and phenylacetonitrile. Patent; Emery Industries, Inc.; US4328168; (1982); (A1) English View in Reaxys Patent; Emery Industries, Inc.; US4328169; (1982); (A1) English View in Reaxys Specific examples of the oxime sulfonate-based acid generator include ... α-(isopropylsulfonyloxyimino)-1-cycloohexenylacetonitrile, α-(n-butylsulfonyloxyimino)-1-cyclohexenylacetonitrile, α-(methylsulfonyloxyimino)-phenylacetonitrile, α-(methylsulfonyloxyimino)-p-methoxyphenylacetonitrile, α-(trifluoromethylsulfonyloxyimo)-phenylacetonitrile, α-(trifluoromethylsulfonyloxyimino)-p-methoxyphenylacetonitrile, α-(ethylsulfonyloxyimino)-p-methoxyphenylacetonitrile, α-(propylsulfonyloxyimino)-p-methylphenylacetonitrile, and ... Patent; Tokyo Ohka Kogyo Co., Ltd.; US7820360; (2010); (B2) English View in Reaxys

14C

Rx-ID: 7179410 View in Reaxys 382/395 Yield

Conditions & References PhCH2Cl, NaCN Binns et al.; Journal of the Chemical Society [Section] C: Organic; (1970); p. 2063,2069 View in Reaxys Benzylchlorid, K14CN Blackburn; Burghard; Journal of Labelled Compounds; vol. 2; (1966); p. 62,66 View in Reaxys K14CN, Benzylchlorid Koltai et al.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 15; (1978); p. 331,334 View in Reaxys aus KCN-14C, Benzylchlorid Wiberg et al.; Journal of Organic Chemistry; vol. 37; (1972); p. 3229,3234 View in Reaxys Benzylbromid, K14CN Wijngaarden; Soudijn; Journal of Labelled Compounds; vol. 1; (1965); p. 207,209 View in Reaxys Benzylchlorid, 14C-KCN, NaCN in DMSO

118/122

2016-03-14 02:10:57

Coke et al.; Journal of the American Chemical Society; vol. 91; (1969); p. 1154 View in Reaxys

3-(Indan-2-yloxy)-4-(Methoxybenzyl Cya‐ nide

Rx-ID: 24904517 View in Reaxys 383/395 Yield

Conditions & References

9.2 g (53%) Y : 3-(Indan-2-yloxy)-4-(Methoxybenzyl Cyanide PREPARATION Y 3-(Indan-2-yloxy)-4-(Methoxybenzyl Cyanide 3-(Indan-2-yloxy)-4-methoxybenzyl chloride (17.7 g, 61.4 mmol) is dissolved in 150 ml dimethylsulfoxide and is treated with potassium cyanide (7.9 g, 121.5 mmol). The reaction is stirred at room temperature for 4.5 hours then partitioned between water and ethyl acetate. It is washed 2*H2 O, 2*brine, dried over MgSO4, filtered and concentrated in vacuo. The crude material is purified by flash chromatography (SiO2, 3:1 hexane/ethyl acetate). The appropriate fractions are combined and concentrated in vacuo to afford 9.2 g (53percent) of the benzyl cyanide as a pale yellow solid. 1 H NMR (CDCl , 300 MHz): delta 7.3-7.2 (m, 4H), 6.9 (m, 3H), 5.22 (m, 1H), 3.9 (s, 1H), 3.75 (s, 2H), 3.5-3.2 (m, 4H). 3 Patent; Pfizer Inc.; US5128358; (1992); (A1) English View in Reaxys 2H 2

Rx-ID: 7250106 View in Reaxys 384/395 Yield

Conditions & References Dilithioderivat 1'', D2O Kaiser,E.M. et al.; Journal of the American Chemical Society; vol. 93; nb. 17; (1971); p. 4237 - 4242 View in Reaxys Benzylcyanid, NaOD, Bzl. Hall,J.H.; Wojciechowska,M.; Journal of Organic Chemistry; vol. 43; (1978); p. 3348 - 3353 View in Reaxys nicht deuterierte Vbg., D2O an Al2O3 Senn et al.; Journal of the American Chemical Society; vol. 87; (1965); p. 680 View in Reaxys

Cl O

F F F

Rx-ID: 25059990 View in Reaxys 385/395 Yield

Conditions & References 1.b : EXAMPLE 1 (b) 9 g of the 4-(2'-chloro-4'-trifluoromethylphenoxy)-benzyl chloride obtained in (a), 2 g of finely powdered sodium cyanide, a trace of sodium iodide and 30 ml of acetone are refluxed for 24 hours in a three-necked flask. The reaction mixture is cooled and precipitated sodium chloride is removed by filtration. The filtrate is washed with acetone and the acetonic solution is concentrated in vacuo. The residue is subjected to vacuum distillation, affording 7.7 g of the benzyl cyanide of the formula STR9 Boiling point: 156° C./0.01 mm. Patent; Ciba-Geigy Corporation; US4353736; (1982); (A1) English

119/122

2016-03-14 02:10:57

View in Reaxys 2H

Rx-ID: 7388407 View in Reaxys 386/395 Yield

Conditions & References Phenylacetamid, 1) n-BuLi, 2) D2O Kaiser et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 3640,3643 View in Reaxys aus Phenyl-acetonitril, sd. D2O, <Na2CO3> Barfield; Grant; Journal of the American Chemical Society; vol. 85; (1963); p. 1899,1903 View in Reaxys H C– Na +

Rx-ID: 8242194 View in Reaxys 387/395 Yield

Conditions & References Phenylacetonitril, NaNH2 Portoghese et al.; Journal of Medicinal Chemistry; vol. 11; nb. 2; (1968); p. 219 View in Reaxys Phenylacetonitril, Naphthyl-natrium in THF; neben anderen Verbb. Bank; Thomas; Tetrahedron Letters; (1973); p. 305 View in Reaxys 2H

2H 2H

Rx-ID: 7658533 View in Reaxys 388/395 Yield

Conditions & References Aus Benzylbromid-d7 mit NaCN/D2O Hinrichs; Kurreck; Niemeier; Tetrahedron; vol. 30; nb. 2; (1974); p. 315 - 320 View in Reaxys /BRN= 960353/, KCN, C2H5OH Aboul-Enein; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 13; (1977); p. 509,510,512 View in Reaxys

C N

Rx-ID: 7593726 View in Reaxys 389/395 Yield

Conditions & References 1,3,2-Dioxaphosph(V)olan, hν Petrellis; Griffin; Chemical Communications (London); (1968); p. 1099 View in Reaxys 1,2-Epoy-1,2-dicyan-1,2-diphenyl-aethan, Trimethyl-aethylen, Photolyse (neben Benzoylcyanid)

120/122

2016-03-14 02:10:57

Temnikova et al.; Journal of Organic Chemistry USSR (English Translation); vol. 3; (1967); p. 1666; Zhurnal Organicheskoi Khimii; vol. 3; (1967); p. 1708 View in Reaxys 1,2-Epoy-1,2-dicyan-1,2-diphenyl-aethan, Tetramethyl-aethylen, Photolyse (neben Benzoylcyanid) Temnikova et al.; Journal of Organic Chemistry USSR (English Translation); vol. 3; (1967); p. 1666; Zhurnal Organicheskoi Khimii; vol. 3; (1967); p. 1708 View in Reaxys H C– N

Rx-ID: 7022422 View in Reaxys 390/395 Yield

Conditions & References Nitril (1A), NaNH2 Albagnac et al.; Bulletin de la Societe Chimique de France; (1974); p. 1469,1470 View in Reaxys aus Phenylacetonitril und Dimsyl-Na Bradamaule et al.; Journal of the Chemical Society, Chemical Communications; (1976); p. 478 View in Reaxys

S B N

Rx-ID: 8349537 View in Reaxys 391/395 Yield

Conditions & References PhCH2C-=N, BBu2SBu Mukaiyama,T. et al.; Tetrahedron Letters; (1971); p. 1097 - 1100 View in Reaxys

13C

Rx-ID: 7389204 View in Reaxys 392/395 Yield

Conditions & References <5-13C>-Benzyltetrazol, Pyrolyse Crow; McNab; Australian Journal of Chemistry; vol. 32; (1979); p. 123,125,131 View in Reaxys

Rx-ID: 7178060 View in Reaxys 393/395 Yield

Conditions & References α-Bromtoluol-3-3H, KCN Blackburn; Burghard; Journal of Labelled Compounds; vol. 2; (1966); p. 62,66 View in Reaxys

121/122

2016-03-14 02:10:57

14C 2

Rx-ID: 7179409 View in Reaxys 394/395 Yield

Conditions & References entspr. Bromid u. KCN Hsi; Journal of Labelled Compounds; vol. 9; (1973); p. 91 View in Reaxys

Cl Al

Rx-ID: 8348248 View in Reaxys 395/395 Yield

Conditions & References Al(CH3)Cl2, C6H5CH2CN Pasynkiewicz et al.; Justus Liebigs Annalen der Chemie; (1975); p. 636,640 View in Reaxys

122/122

2016-03-14 02:10:57