Emmert reaction

The Emmert reaction is a name reaction from the field of organic chemistry . This reaction was originally described by the chemists Bruno Emmert and Erich Asendorf in 1939 and is used for the production of 2-pyridine-dialkylcarbinol.

Overview reaction

The Emmert reaction is used to produce 2-pyridine-dialkylcarbinol 3 by reacting pyridine 1 and a ketone 2 in the presence of aluminum or magnesium amalgam .

Individual evidence

↑ B. Emmert and E. Asendorf: A synthesis of α ‐ pyridyl ‐ dialkyl ‐ carbinolen , E., Reports of the German Chemical Society , 1939, 72, 1188, doi: 10.1002 / cber.19390720610 .
↑ (a) Sheinkman, AK; Nelin, EN; Luk'yanenko, LV and Klyuev, NA, Zh. Org. Khim. , 1978, 14, 2542.
(b) Tschesche, R. and Fuehrer, W., Chem. Ber. , 1978, 111, 3502.
(c) Sheinkman, AK; Potashnikova, SG and Baranov, SN, Zh. Org. Khim. , 1971, 7, 1550.
(d) Russell, CA; Crawforth, CE and Meth-Cohn, O., J. Chem. Soc. D , 1970, 1406.
(e) Bachman, GB; Hamer, M .; Dunning, E. and Schisla, RM: Heterogeneous Bimolecular Reduction. I. General Considerations of Mechanism. The Emmert Reaction , J. Org. Chem. , 1957, 22, 1296-1302, doi: 10.1021 / jo01362a003 .
(f) Lochte, HL; Kruse, PF and Wheeler, EN: The Emmert Reaction in the Synthesis of Alkyl- and Cycloalkylpyridines , J. Am. Chem. Soc. , 1953, 75, 4477-4481, doi: 10.1021 / ja01114a024 .
^ Zerong Wang: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , pp. 993 , doi : 10.1002 / 9780470638859 ( wiley.com ).

[1] B. Emmert and E. Asendorf: A synthesis of α ‐ pyridyl ‐ dialkyl ‐ carbinolen , E., Reports of the German Chemical Society , 1939, 72, 1188, doi: 10.1002 / cber.19390720610 .

[2] (a) Sheinkman, AK; Nelin, EN; Luk'yanenko, LV and Klyuev, NA, Zh. Org. Khim. , 1978, 14, 2542.
(b) Tschesche, R. and Fuehrer, W., Chem. Ber. , 1978, 111, 3502.
(c) Sheinkman, AK; Potashnikova, SG and Baranov, SN, Zh. Org. Khim. , 1971, 7, 1550.
(d) Russell, CA; Crawforth, CE and Meth-Cohn, O., J. Chem. Soc. D , 1970, 1406.
(e) Bachman, GB; Hamer, M .; Dunning, E. and Schisla, RM: Heterogeneous Bimolecular Reduction. I. General Considerations of Mechanism. The Emmert Reaction , J. Org. Chem. , 1957, 22, 1296-1302, doi: 10.1021 / jo01362a003 .
(f) Lochte, HL; Kruse, PF and Wheeler, EN: The Emmert Reaction in the Synthesis of Alkyl- and Cycloalkylpyridines , J. Am. Chem. Soc. , 1953, 75, 4477-4481, doi: 10.1021 / ja01114a024 .

[3] Zerong Wang: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , pp. 993 , doi : 10.1002 / 9780470638859 ( wiley.com ).