The Michael Reaction

Thomas Poon

W. M. Keck Science Center, Claremont McKenna, Pitzer, and Scripps Colleges, Claremont, CA 91711-5916

Bradford P. Mundy and Thomas W. Shattuck

Department of Chemistry, Colby College, Waterville, ME 04901

Abstract

A brief account of the Michael reaction is provided, illustrating its versatility as a topic in undergraduate chemistry courses. Included is a short biography of the reaction's namesake, examples of its use in organic synthesis, and its unique role in the defense mechanism of the bacterium Micromonospora echinospora. A computational rationale for the selectivity of 1,4 versus 1,2 addition of nucleophiles to -unsaturated carbonyls is discussed and links to animations suitable for an introductory organic chemistry course are provided.

Journal of Chemical Education, 2002, 79, 264                       Full text (PDF) | Supplement

-- SiripornJu - 08 Mar 2007