Reaxys
PubChem
eMolecules
Reactions (26)
Yield
Substances (2)
Citations (28)
Conditions
References
1
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With tetramethyl-α-iodoenamine in chloroform-d1
T=20°C; Inert atmosphere; Hide Experimental Procedure
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Rx-ID: 41592958 Find similar reactions
Munyemana, Franois; George, Isabelle; Devos, Alain; Colens, Alain; Badarau, Eduard; Frisque-Hesbain, Anne-Marie; Loudet, Aurore; Differding, Edmond; Damien, Jean-Marie; Rmion, Jeanine; Van Uytbergen, Jacqueline; Ghosez, Lon
Tetrahedron, 2016 , vol. 72, # 3 p. 420 - 430 Title/Abstract Full Text View citing articles Show Details
4.2. General procedures for the reaction of a-haloenamines with oxyacids and alcohols
General procedure: Reactions were performed under dry argon atmosphere under magnetic stirring. In procedure A, the alcohol was introduced through a syringe into a 0.5-1 M solution of the α-haloenamine (usually 1.1 equiv) in freshly dried chloroform or dichloromethane or the corresponding deuterated solvents. The reactions were quite exothermic. When performed on a preparative scale, the alcoholwas added at 0 °C, and then the mixture was left at room temperaturefor 0.5-3 h. In procedure B, the α-haloenamine was introduced into a solution of alcohol in the same solvents at 0 °C. It was shown that both procedures gave identical results. In few cases involving the preparation of unstable halides, the halogenation was effected at lower temperature (see Scheme 3) for up to 4 h. Yields were determined after removal of the solvent either by 1H NMR using an added standard (usually benzene or toluene) or by GLC. In some cases the halides were purified by distillation or flash chromatography. The isolated yields were always very close to those measured by NMR or GLC. Most of the halogenation products obtained in this study were known compounds: their spectroscopic properties have been shown to be identical to those reported in the literature and will therefore not been reported here. A
B
2
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Rx-ID: 36348088 Find similar reactions
With copolymer supported Rh nanoparticles; copolymer supported iodide species T=120°C; P=22502.3 Torr; Autoclave;
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Li, Fengbo; Chen, Bingfeng; Huang, Zhijun; Lu, Tao; Yuan, Yin; Yuan, Guoqing
Green Chemistry, 2013 , vol. 15, # 6 p. 1600 - 1607 Title/Abstract Full Text View citing articles Show Details
A
B
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3
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Rx-ID: 9738304 Find similar reactions
A: 18% B: 34%
in dichloromethane
3 h; Heating;
Voronkov; Trukhina; Vlasova
Russian Journal of Organic Chemistry, 2004 , vol. 40, # 3 p. 357 - 359 Title/Abstract Full Text View citing articles Show Details
A
B
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4
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A: 5% B: 95%
With trimethylsilyl iodide; iodine in chloroform-d1
T=50°C; 2 h;
Keinan, E.; Sahai, M.
Journal of Organic Chemistry, 1990 , vol. 55, # 12 p. 3922 - 3926 Title/Abstract Full Text View citing articles Show Details
A: 5% B: 95%
With trimethylsilyl iodide; iodine in chloroform-d1
T=50°C; 1.15 h;
Keinan, E.; Sahai, M.
Journal of Organic Chemistry, 1990 , vol. 55, # 12 p. 3922 - 3926 Title/Abstract Full Text View citing articles Show Details
A
B
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5
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A: 80% B: 10%
With diiodo monosilane; iodine in chloroform-d1
T=50°C; 15 h;
Keinan, E.; Sahai, M.
Journal of Organic Chemistry, 1990 , vol. 55, # 12 p. 3922 - 3926 Title/Abstract Full Text View citing articles Show Details
A: 40% B: 35%
With diiodo monosilane; iodine in chloroform-d1
T=50°C; 2.5 h;
Keinan, E.; Sahai, M.
Journal of Organic Chemistry, 1990 , vol. 55, # 12 p. 3922 - 3926 Title/Abstract Full Text View citing articles Show Details
6
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With diiodo monosilane; iodine in chloroform-d1
T=50°C; 15 h;
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Rx-ID: 1933043 Find similar reactions
Keinan, E.; Sahai, M.
Journal of Organic Chemistry, 1990 , vol. 55, # 12 p. 3922 - 3926 Title/Abstract Full Text View citing articles Show Details
A
B
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7
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Rx-ID: 1933044 Find similar reactions
A: 66% B: 32%
8
With diiodo monosilane; iodine in chloroform-d1
T=50°C; 1.5 h;
Rx-ID: 1934615 Find similar reactions
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With trimethylsilyl iodide; iodine in chloroform-d1
T=50°C; 2 h;
Keinan, E.; Sahai, M.
Journal of Organic Chemistry, 1990 , vol. 55, # 12 p. 3922 - 3926 Title/Abstract Full Text View citing articles Show Details
A: 6% B: 94%
With trimethylsilyl iodide; iodine in chloroform-d1
T=50°C; 2 h;
Keinan, E.; Sahai, M.
Journal of Organic Chemistry, 1990 , vol. 55, # 12 p. 3922 - 3926 Title/Abstract Full Text View citing articles Show Details
A
B
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Rx-ID: 1934616 Find similar reactions
B
A: 6% B: 94%
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A
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9
Keinan, E.; Sahai, M.
Journal of Organic Chemistry, 1990 , vol. 55, # 12 p. 3922 - 3926 Title/Abstract Full Text View citing articles Show Details
A: 58% B: 34%
With diiodo monosilane; iodine in chloroform-d1
T=50°C; 15 h;
Keinan, E.; Sahai, M.
Journal of Organic Chemistry, 1990 , vol. 55, # 12 p. 3922 - 3926 Title/Abstract Full Text View citing articles Show Details
A: 58% B: 34%
With diiodo monosilane; iodine in chloroform-d1
T=50°C; 15 h;
Keinan, E.; Sahai, M.
Journal of Organic Chemistry, 1990 , vol. 55, # 12 p. 3922 - 3926 Title/Abstract Full Text View citing articles Show Details
10
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82%
With diiodo monosilane; iodine in chloroform-d1
T=50°C; 7 h;
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Rx-ID: 3555508 Find similar reactions
Keinan, E.; Sahai, M.
Journal of Organic Chemistry, 1990 , vol. 55, # 12 p. 3922 - 3926 Title/Abstract Full Text View citing articles Show Details
11
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With iodine in dichloromethane
byproducts: (P(C6H5)3)2PdCl2; addition of I2 to Pd(P(C6H5)3)2(CH3CO)Cl in CH2Cl2; determination : IR;
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Rx-ID: 26517308 Find similar reactions
Kubota, Mitsuru; Boegeman, Scott C.; Keil, Robert N.; Webb, Carl G.
Organometallics, 1989 , vol. 8, p. 1616 - 1620 Full Text View citing articles Show Details
12
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With iodine in dichloromethane
byproducts: (PPh)2PtClI; addition of I2 to trans(Pt(PPh3)2(CH3CO)Cl) in CH2Cl2; determination:IR;
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Rx-ID: 26629913 Find similar reactions
Kubota, Mitsuru; Boegeman, Scott C.; Keil, Robert N.; Webb, Carl G.
Organometallics, 1989 , vol. 8, p. 1616 - 1620 Full Text View citing articles Show Details
A
B
13
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With carbon monoxide in 1,4-dioxane; water
heated at 100°C for 3 h under an atmosphere of CO; detn. by (31)P-NMR and GC (hydrolysis of CH3C(O)I to acetic acid);
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Lindner, Ekkehard; Andres, Berthold
Chemische Berichte, 1988 , vol. 121, p. 829 - 832 Title/Abstract Full Text Show Details
14
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46%
With trimethylsilyl iodide
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Rx-ID: 693089 Find similar reactions
Schmidt, Arthur H.; Russ, Manuel; Grosse, Detlef
Synthesis, 1981 , # 3 p. 216 - 218 Title/Abstract Full Text Show Details
With pyridine; Bu3SnI
T=40°C; Thermodynamic dataEquilibrium constant;
Friedrich, Edwin C.; Abma, Charles B.
Journal of the American Chemical Society, 1980 , vol. 102, # 4 p. 1367 - 1371 Title/Abstract Full Text View citing articles Show Details
With hydrogen iodide
Staudinger; Anthes
Chemische Berichte, 1913 , vol. 46, p. 1435 Full Text Show Details
Hide Details
With CaI2
With sodium iodide in acetonitrile
Spindler
Justus Liebigs Annalen der Chemie, 1885 , vol. 231, p. 272 Full Text Show Details
Belsner, Klaus; Hoffmann, H. M. R.
Synthesis, 1982 , # 3 p. 239 - 240 Title/Abstract Full Text Show Details
A
B
15
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Rx-ID: 1336135 Find similar reactions
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Bigler,P.; Neuenschwander,M.
Helvetica Chimica Acta, 1978 , vol. 61, p. 2165 - 2175 Full Text View citing articles Show Details
in chloroform-d1
T=20°C; Equilibrium constant;
16
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Rx-ID: 6950590 Find similar reactions
Hide Experimental Procedure
Moloney; Krisher
Journal of Chemical Physics, 1966 , vol. 45, p. 3277,3280 Full Text Show Details
Teijin Limited
Patent: US4009196 A1, 1977 ; Title/Abstract Full Text Show Details
Specific examples of these acid halides and acid anhydrides are shown below. Ii-1-a. acid Halides Acetyl chloride, acetyl bromide, acetyl iodide, acetyl fluoride, propionyl chloride, propionyl bromide, n-butyryl chloride, isobutyryl chloride, n-valeryl chloride, ...
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Examples of an acid halide of the Formula III or IV are as follows: Acetyl chloride
Sumitomo Chemical Company, Limited
Patent: US4055565 A1, 1977 ; Title/Abstract Full Text Show Details
Acetyl bromide Acetyl iodide Chloroacetyl chloride Bromoacetyl chloride Propionyl chloride Butyryl chloride Isobutyryl chloride Cyclohexane carbonyl chloride ...
17
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With diethyl ether; hydrogen iodide
T=10°C;
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Rx-ID: 115860 Find similar reactions
Eastman Kodak Co.
Patent: US2475966 , 1945 ; Full Text Show Details
18
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Rx-ID: 6950591 Find similar reactions
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Gorin
Journal of Chemical Physics, 1939 , vol. 7, p. 258 Full Text Show Details
Nicholson
Journal of Chemical Physics, vol. 20, p. 1811 Full Text Show Details
Benson; Forbes
Journal of the American Chemical Society, 1943 , vol. 65, p. 1403 Full Text Show Details
Gorin
Acta physicoch.U.R.S.S., vol. 8, p. 513 Chem. Zentralbl., 1938 , vol. 109, # II p. 287 Full Text Show Details
A
B
19
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With potassium iodide in further solvent(s) solvent: BF3 etherate;
Seel, F.
Z. Anorg. Chem., 1943 , vol. 250, p. 331 - 351 Full Text Show Details
With KI in further solvent(s) solvent: BF3 etherate;
Gmelin Handbook: B: SVol.1, 4.4.5, page 187 - 196 Full Text Show Details
20
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With hydrogen iodide; carbon
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Rx-ID: 60170 Find similar reactions
Eschenbach
Patent: DE638441 , 1935 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 23, p. 74 Full Text Show Details
A
B
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21
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Job; Reich; Vergnaud
Bulletin de la Societe Chimique de France, 1924 , vol. <4>35, p. 1409 Full Text Show Details
22
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Rx-ID: 5804248 Find similar reactions
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Staudinger; Anthes
Chemische Berichte, 1913 , vol. 46, p. 1435 Full Text Show Details
23
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With phosphorus; iodine
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Rx-ID: 572499 Find similar reactions
Guthrie
Justus Liebigs Annalen der Chemie, 1857 , vol. 103, p. 335 Full Text Show Details
Thiele; Haakh
Justus Liebigs Annalen der Chemie, 1909 , vol. 369, p. 144 Full Text Show Details
24
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Rx-ID: 5463091 Find similar reactions
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Guthrie
Justus Liebigs Annalen der Chemie, 1857 , vol. 103, p. 335 Full Text Show Details
Thiele; Haakh
Justus Liebigs Annalen der Chemie, 1909 , vol. 369, p. 144 Full Text Show Details
25
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Rx-ID: 5804249 Find similar reactions
Spindler
Justus Liebigs Annalen der Chemie, 1902 , vol. 321, p. 272 Full Text Show Details
26
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durch Destillation;
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Rx-ID: 534612 Find similar reactions
Cahours
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1857 , vol. 44, p. 1255 Justus Liebigs Annalen der Chemie, 1857 , vol. 104, p. 111 Full Text Show Details