Organic Chemistry Portal



Practical Approach to α- or γ-Heterosubstituted Enoic Acids

Julia L. Shamshina and Timothy S. Snowden*

*Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa, Alabama 34587-0336, Email:

J. L. Shamshina, T. S. Snowden, Org. Lett., 2006, 8, 5881-5884.

DOI: 10.1021/ol0625132

see article for more reactions


The reaction of alkenyl trichloromethyl carbinols with various nucleophiles under protic basic conditions reveals that mercaptans participate by α-substitution (SN2), wheareas hydroxide prefers γ-substitution with stereoselective allylic transposition (SN2'). Regioselectivity with alkoxides depends upon alkene substitution.

see article for more examples

proposed mechanism

General and Practical Conversion of Aldehydes to Homologated Carboxylic Acids

L. R. Cafiero, T. S. Snowden, Org. Lett., 2008, 10, 3853-3856.

Key Words

Jocic Reaction, Carboxylic Acids, α-Hydroxy acids

ID: J54-Y2006-3980