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: snowdenbama.ua.edu
J. L. Shamshina, T. S. Snowden, Org. Lett., 2006, 8, 5881-5884.
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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.
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General and Practical Conversion of Aldehydes to Homologated Carboxylic Acids
L. R. Cafiero, T. S. Snowden, Org. Lett., 2008, 10, 3853-3856.
Jocic Reaction, Carboxylic Acids, α-Hydroxy acids