7. Piperidine hydrobromide

Page 1

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PubChem

eMolecules

Reactions (31)

Yield

Substances (2)

Citations (21)

Conditions

References

1

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Rx-ID: 20744155 Find similar reactions

Multi-step reaction with 2 steps 1: acetonitrile / 1 h / Ambient temperature 2: 17 percent / acetonitrile / 16 h / Heating View Scheme

Kanner,C.B.; Pandit,U.K.

Tetrahedron, 1982 , vol. 38, p. 3597 Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1.1: potassium carbonate / methanol / 20 °C 1.2: 1 h 2.1: hydrogen bromide / methanol; water; isopropyl alcohol / 4 h 3.1: aq. acetate buffer / pH 5.6 / |Irradiation View Scheme

Bownik, Iwona; ebej, Peter; Literk, Jaromr; Heger, Dominik; imek, Zdenk; Givens, Richard S.; Kln, Petr

Journal of Organic Chemistry, 2015 , vol. 80, # 19 p. 9713 - 9721 Title/Abstract Full Text View citing articles Show Details

A

B


2

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Rx-ID: 41128615 Find similar reactions

Multi-step reaction with 2 steps 1: hydrogen bromide / methanol; water; isopropyl alcohol / 4 h 2: aq. acetate buffer / pH 5.6 / |Irradiation View Scheme

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Bownik, Iwona; ebej, Peter; Literk, Jaromr; Heger, Dominik; imek, Zdenk; Givens, Richard S.; Kln, Petr

Journal of Organic Chemistry, 2015 , vol. 80, # 19 p. 9713 - 9721 Title/Abstract Full Text View citing articles Show Details

A

B

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3

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A: 99% B: 99%

Bownik, Iwona; ebej, Peter; Literk, Jaromr; Heger, Dominik; imek, Zdenk; Givens, Richard S.; Kln, Petr

Journal of Organic Chemistry, 2015 , vol. 80, # 19 p. 9713 - 9721 Title/Abstract Full Text View citing articles Show Details

in aq. acetate buffer pH=5.6; Irradiation; pH-value;

A

B

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4

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A: 66% B: 22%

in 1,4-dioxane

2 h; Reflux; Hide Experimental Procedure

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Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract Full Text View citing articles Show Details


2:General procedure for the synthesis of 5

General procedure: A mixture of alkyl 3-chloro(or bromo)-2-oxo-3-arylpropanoate 2 (3.0 mmol), 1-cyclohexenylpiperidine (or 4-tert-butyl-1-cyclohexenylpiperidine) 4a(b) (5.2 mmol) and dioxane (30 mL) was heated at reflux for 2 h. After cooling down to room temperature, the precipitate was filtered and recrystallized in toluene (or washed with i-PrOH) to give piperidinium chloride (or bromide) 6. The solvent was removed to give a slightly brown crude product 5, which was purified on column chromatography with silica gel (eluent-hexane/EtOAc).

5

Rx-ID: 41255188 Find similar reactions

B

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A

Multi-step reaction with 2 steps 1: 1,4-dioxane / 2 h / |Reflux 2: 1,4-dioxane / 2 h / |Reflux View Scheme

Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 1,4-dioxane / 2 h / |Reflux 2: 1,4-dioxane / 2 h / |Reflux View Scheme

Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 1,4-dioxane / 2 h / |Reflux 2: 1,4-dioxane / 2 h / |Reflux View Scheme

Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract Full Text View citing articles Show Details

Hide Details

Multi-step reaction with 2 steps 1: 1,4-dioxane / 2 h / |Reflux 2: 1,4-dioxane / 2 h / |Reflux View Scheme

Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 1,4-dioxane / 2 h / |Reflux 2: 1,4-dioxane / 2 h / |Reflux View Scheme

Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 1,4-dioxane / 2 h / |Reflux 2: 1,4-dioxane / 2 h / |Reflux View Scheme

Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 1,4-dioxane / 2 h / |Reflux 2: 1,4-dioxane / 2 h / |Reflux View Scheme

Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 1,4-dioxane / 2 h / |Reflux 2: 1,4-dioxane / 2 h / |Reflux View Scheme

Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract Full Text View citing articles Show Details


6

B

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7

A

Multi-step reaction with 2 steps 1: 1,4-dioxane / 2 h / |Reflux 2: 1,4-dioxane / 2 h / |Reflux View Scheme

Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract Full Text View citing articles Show Details

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B

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Rx-ID: 41255206 Find similar reactions

A: 78% B: 12%

Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract Full Text View citing articles Show Details

in 1,4-dioxane

2 h; Reflux; Hide Experimental Procedure

3:General procedure for the synthesis of 5

General procedure: A mixture of alkyl 3-chloro(or bromo)-2-oxo-3-arylpropanoate 2 (3.0 mmol), 1-cyclohexenylpiperidine (or 4-tert-butyl-1-cyclohexenylpiperidine) 4a(b) (5.2 mmol) and dioxane (30 mL) was heated at reflux for 2 h. After cooling down to room temperature, the precipitate was filtered and recrystallized in toluene (or washed with i-PrOH) to give piperidinium chloride (or bromide) 6. The solvent was removed to give a slightly brown crude product 5, which was purified on column chromatography with silica gel (eluent-hexane/EtOAc).

8

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WYETH; SIENA BIOTECH S.P.A.; HAYDAR, Simon, N.; BOTHMANN, Hendrick; GHIRON, Chiara; MACCARI, Laura; MICCO, Iolanda; NENCINI, Arianna; ZANALETTI, Riccardo

Patent: WO2010/9290 A1, 2010 ; Location in patent: Page/Page column 134 ;

in toluene

10 h; Reflux; Hide Experimental Procedure

Title/Abstract Full Text Show Details

10.a:

Example 10N-[5-(4-Methoxy-phenyl)-2H-pyrazol-3-yl]-4-piperidin-l-yl-butyramide a) 4-Piperidin-l-yl-butyric acid ethyl ester; [0357] To a solution of piperidine (5.4 g, 65 mmol) in toluene (15 mL) ethyl 4- bromobutyrate (3.8 mL, 26 mmol) was added and the reaction mixture was refluxed for 10 hours. The mixture was allowed to cool down to room temperature and the white solid present (piperidium bromide) was filtered off and washed with ether. The filtrate was concentrated under reduced pressure to give the title product which was used in the next step without further purification.C11H21NO2 Mass (calculated) [199]; (found) [M+H+] =200LC Rt =

0.2, 100percent (5 min method)1H-NMR (400 MHz, MeOH-d4): 1.22-1.25 (3H, m), 1.46-1.47 (2H, m), 1.57-1.63 (4H, m), 1.78-1.84 (2H, m), 2.30-2.35 (4H, m), 2.42 (4H, m, broad), 4.08-4.14 (2H, m).

9

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Rx-ID: 26517260 Find similar reactions

A: 43%

in tetrahydrofuran

inert atmosphere; partial evapn., filtn., addn. of hexane, filtn., washing, drying; elem. anal.;

Wenschuh, E.; Zimmering, R.

Zeitschrift fuer Anorganische und Allgemeine Chemie, 1989 , vol. 570, p. 93 - 101 Full Text Show Details

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10

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in acetonitrile

T=55°C; Rate constantMechanism;

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Kravchenko, V. V.; Kotenko, A. A.; Popov, A. F.; Kostenko, L. I.; Vegh, D.; Kovac, J.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, # 11 p. 2140 - 2143 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 11 p. 2374 - 2377 Title/Abstract Full Text Show Details

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11

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Rx-ID: 1484853 Find similar reactions

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Titskii, G. D.; Mitchenko, E. S.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, # 10 p. 1949 - 1954 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 10 p. 2161 - 2166 Title/Abstract Full Text Show Details

in acetonitrile

T=25°C; Rate constant;

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12

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Rx-ID: 1484896 Find similar reactions

Kravchenko, V. V.; Kotenko, A. A.; Popov, A. F.; Kostenko, L. I.; Vegh, D.; Kovac, J.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, # 11 p. 2140 - 2143 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 11 p. 2374 - 2377 Title/Abstract Full Text Show Details

in acetonitrile

T=55°C; Rate constantMechanism;

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13

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A: 12.7 g

in acetonitrile

T=2 - 5°C; 24 h;

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Popov, A. F.; Anikeev, A. V.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, # 5 p. 939 - 944 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 5 p. 1040 - 1046


Title/Abstract Full Text Show Details

With acetic acid in cyclohexane

T=30°C; other concentrations, other catalyst; Rate constantMechanism;

Popov, A. F.; Anikeev, A. V.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, # 5 p. 939 - 944 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 5 p. 1040 - 1046 Title/Abstract Full Text Show Details

in acetonitrile

T=2 - 5°C; 24 h;

Popov, A. F.; Anikeev, A. V.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, # 5 p. 939 - 944 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 5 p. 1040 - 1046 Title/Abstract Full Text Show Details

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14

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Rx-ID: 1482224 Find similar reactions

Popov, A. F.; Piskunova, Z.; Matvienko, V. N.

Journal of Organic Chemistry USSR (English Translation), 1986 , vol. 22, # 7 p. 1299 - 1302 Zhurnal Organicheskoi Khimii, 1986 , vol. 22, # 7 p. 1442 - 1446 Title/Abstract Full Text Show Details

in acetonitrile

T=25°C; Rate constantMechanism;

A

B

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15

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Rx-ID: 1483108 Find similar reactions

in acetonitrile

T=25°C; the effect of steric and electronic structure of the amine; Rate constantProduct distributionMechanism;

Litvinenko, L. M.; Titskii, G. D.; Mitchenko, E. S.

Journal of Organic Chemistry USSR (English Translation), 1983 , vol. 19, p. 1731 - 1736 Zhurnal Organicheskoi Khimii, 1983 , vol. 19, # 9 p. 1970 - 1975 Title/Abstract Full Text Show Details

A

B

C


16

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Rx-ID: 1483520 Find similar reactions

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B: 15% C: 4%

With palladium diacetate; tris-(o-tolyl)phosphine

T=100°C;

Shi, L.; Narula, C. K.; Mak, K. T.; Kao, L.; Xu, Y.; Heck, R. F.

Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 3894 - 3900 Title/Abstract Full Text View citing articles Show Details

B: 15% C: 4%

With palladium diacetate; tris-(o-tolyl)phosphine

T=100°C;

Shi, L.; Narula, C. K.; Mak, K. T.; Kao, L.; Xu, Y.; Heck, R. F.

Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 3894 - 3900 Title/Abstract Full Text View citing articles Show Details

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C

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17

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B: 33% C: 11%

With palladium diacetate; tris-(o-tolyl)phosphine

T=100°C;

Shi, L.; Narula, C. K.; Mak, K. T.; Kao, L.; Xu, Y.; Heck, R. F.

Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 3894 - 3900 Title/Abstract Full Text View citing articles Show Details

B: 33% C: 11%

With palladium diacetate; tris-(o-tolyl)phosphine

T=100°C;

Shi, L.; Narula, C. K.; Mak, K. T.; Kao, L.; Xu, Y.; Heck, R. F.

Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 3894 - 3900 Title/Abstract Full Text View citing articles Show Details

A

18

B

C


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Rx-ID: 1483548 Find similar reactions

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B: 38% C: 38%

With palladium diacetate; tris-(o-tolyl)phosphine

T=100°C;

Shi, L.; Narula, C. K.; Mak, K. T.; Kao, L.; Xu, Y.; Heck, R. F.

Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 3894 - 3900 Title/Abstract Full Text View citing articles Show Details

B: 38% C: 38%

With palladium diacetate; tris-(o-tolyl)phosphine

T=100°C;

Shi, L.; Narula, C. K.; Mak, K. T.; Kao, L.; Xu, Y.; Heck, R. F.

Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 3894 - 3900 Title/Abstract Full Text View citing articles Show Details

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B

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19

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Rx-ID: 1484708 Find similar reactions

in acetonitrile

T=25°C; relative rate const. to 2-bromoderivative; Rate constantProduct distributionMechanism;

Litvinenko, L. M.; Titskii, G. D.; Mitchenko, E. S.

Journal of Organic Chemistry USSR (English Translation), 1983 , vol. 19, p. 1731 - 1736 Zhurnal Organicheskoi Khimii, 1983 , vol. 19, # 9 p. 1970 - 1975 Title/Abstract Full Text Show Details

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B

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20

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B: 13%

in diethyl ether

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Cardellach, J.; Estopa, C.; Font, J.; Moreno-Manas, M.; Ortuno, R. M.; et al.

Tetrahedron, 1982 , vol. 38, # 15 p. 2377 - 2394 Title/Abstract Full Text View citing articles Show Details

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B

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Rx-ID: 2398364 Find similar reactions

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A: 58% B: 17%

in acetonitrile

16 h; Heating;

Kanner,C.B.; Pandit,U.K.

Tetrahedron, 1982 , vol. 38, p. 3597 Full Text View citing articles Show Details

A: 58% B: 17%

in acetonitrile

16 h; Heating; Mechanism;

Kanner,C.B.; Pandit,U.K.

Tetrahedron, 1982 , vol. 38, p. 3597 Full Text View citing articles Show Details

A

B

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A: 20.8 g B: 95%

With hydrogen sulfide in ethanol

1.) -60 - 50 deg C, 13 hrs., 2.) -15 deg C, overnight;

Tomchin, A.B.

Journal of Organic Chemistry USSR (English Translation), 1981 , vol. 17, p. 504 - 510 Zhurnal Organicheskoi Khimii, 1981 , vol. 17, # 3 p. 589 - 595 Title/Abstract Full Text Show Details

23

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Multi-step reaction with 3 steps 1: 89.1 percent / sulfur / 1 h / Heating

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Rx-ID: 11700257 Find similar reactions

Tomchin, A.B.

Journal of Organic Chemistry USSR (English Translation), 1981 , vol. 17, p. 504 - 510


2: 76 percent / benzene / standing overnight 3: 20.8 g / H2S (gas) / ethanol / 1.) -60 - 50 deg C, 13 hrs., 2.) -15 deg C, overnight View Scheme

Zhurnal Organicheskoi Khimii, 1981 , vol. 17, # 3 p. 589 - 595 Title/Abstract Full Text Show Details

24

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Multi-step reaction with 2 steps 1: 76 percent / benzene / standing overnight 2: 20.8 g / H2S (gas) / ethanol / 1.) -60 - 50 deg C, 13 hrs., 2.) -15 deg C, overnight View Scheme

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Rx-ID: 11708503 Find similar reactions

Tomchin, A.B.

Journal of Organic Chemistry USSR (English Translation), 1981 , vol. 17, p. 504 - 510 Zhurnal Organicheskoi Khimii, 1981 , vol. 17, # 3 p. 589 - 595 Title/Abstract Full Text Show Details

25

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Rx-ID: 25223504 Find similar reactions

Warner-Lambert Company

Patent: US3971794 A1, 1976 ; Title/Abstract Full Text Show Details

1:3-Methyl-4-oxo-5N-piperidino-thiazolidin-2-ylidene-acetic acid

141 g. ethyl tert.-butyl-cyanoacetate (b.p. 60°C./1.5 mm.Hg.; n20 1.4180) and 120 cc. ethyl thioglycolate are dissolved in 1 liter benzene, mixed with 140 cc. triethylamine and stirred for 72 hours at ambient temperature. The bulk of the solvent is then distilled off in a vacuum and the solid residue is separated and washed with a little benzene on a suction filter. There is obtained, after air drying, 134 g. (79percent of theory) tert.-butyl 4-oxo-thiazolidin-2-ylidene-acetate which, after recrystallization from isopropanol, melts at 177.4°C. 63.5 g. tert.-butyl 4-oxo-thiazolidin-2-ylidene-acetate and 41.4 g. potassium carbonate are suspended in 250 cc. methanol. The reaction mixture is heated to reflux temperature and mixed dropwise with a solution of 37.8 g. dimethyl sulphate in 50 cc. methanol. After an hour, the reaction is finished. The solvent is removed in a vacuum and the residue introduced into 0.5 liter water. The crude tert.-butyl 3-methyl-4-oxo-thiazolidin-2-ylidene-acetate is taken up in ether and the ethereal phase is then dried and evaporated. The residue is recrystallized from cyclohexane. There is obtained 56 g. (82percent of theory) tert.-butyl (3-methyl-4-oxo-thiazolidin-2-ylidene)-acetate, which melts at 77.4°C. 36.8 g. tert.-butyl 3-methyl-4-oxo-thiazolidin-2-ylidene-acetate is dissolved in 700 cc. anhydrous carbon tetrachloride. Under reflux conditions, there is first introduced 0.3 g. azo-bis-isobutyric acid nitrile and then, within a period of 10 minutes, 29 g. N-bromosuccinimide. After boiling under reflux for 20 minutes, the reaction mixture is filtered and the filtrate is evaporated to dryness in a vacuum. The oily residue is taken up in 0.5 liter benzene, cooled to +5°C. and mixed in several portions with 32 cc. piperidine. After standing for several hours at ambient temperature, the piperidine hydrobromide formed is separated off and the filtrate evaporated in a vacuum. After the addition of 50 cc. isopropanol, the mixture is cooled to 0°C. The precipitated tert.-butyl 3-methyl-4-oxo-5N-piperidino-thiazolidin-2-ylidene-acetate is recrystallized from isopropanol. The yield is 21.5 g. (38percent of theory over 2 stages) and the product melts at 154°C. Analysis: C15 H24 N2 O3 S (M.W. 312.41); calc.: C 57.66percent; H 7.74percent; N 8.97percent; S 10.26percent; found: 57.56percent; 7.80percent; 9.15percent; 10.33percent. A

B

C


26

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Rx-ID: 5724756 Find similar reactions

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Bras; Kore

Zhurnal Obshchei Khimii, 1953 , vol. 23, p. 868,872,873;engl.Ausg.S.909,912,913 Full Text Show Details

6-stdg. Behandeln unter Lichtausschluss;

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B

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27

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Rx-ID: 5579041 Find similar reactions

Cromwell; Cram

Journal of the American Chemical Society, 1943 , vol. 65, p. 301,307 Full Text Show Details

Hydrogenation;

28

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Rx-ID: 7054374 Find similar reactions

in verschiedenen organischen Loesungsmitteln; Kinetics;

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Salomon

Helvetica Chimica Acta, 1933 , vol. 16, p. 1365,1369 Helvetica Chimica Acta, 1936 , vol. 19, p. 765 Full Text Show Details

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29

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Rx-ID: 7054373 Find similar reactions

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Freundlich; Bartels

Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre, 1922 , vol. 101, p. 181 Full Text Show Details

T=0°C; Geschwindigkeit der Umwandlung;

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B

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30

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With hydrogen bromide

v.Braun Chemische Berichte, 1909 , vol. 42, p. 2042 Full Text Show Details

31

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Rx-ID: 17365 Find similar reactions

Delepine

Bulletin de la Societe Chimique de France, 1898 , vol. <3> 19, p. 614 Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1898 , vol. 126, p. 1795 Full Text Show Details

Lellmann; Schwaderer

Chemische Berichte, 1889 , vol. 22, p. 1327 Full Text Show Details


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