General and Practical Conversion of Aldehydes to Homologated Carboxylic Acids
Lauren R. Cafiero and Timothy S. Snowden*
*Department of Chemistry, The University of Alabama, Box
870336, Tuscaloosa, Alabama 35487-0336, Email: snowden
bama.ua.edu
L. R. Cafiero, T. S. Snowden, Org. Lett., 2008, 10, 3853-3856.
DOI: 10.1021/ol8016484
Abstract
The reaction of aldehydes with trichloromethide followed by reductive ring opening under basic conditions affords homologated carboxylic acids in high yields. This operationally simple procedure provides a practical, efficient alternative to other homologation protocols and is compatible with sensitive aldehydes including enals and enolizable substrates.
see article for more examples
proposed reaction pathway
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Preparation of One-Carbon Homologated Amides from Aldehydes or Primary Alcohols
M. K. Gupta, Z. Li, T. S. Snowden, Org. Lett., 2014, 16, 1602-1605.
Practical Approach to α- or γ-Heterosubstituted Enoic Acids
J. L. Shamshina, T. S. Snowden, Org. Lett., 2006, 8, 5881-5884.
Key Words
Jocic Reaction, Trichloromethyl Carbinols, Carboxylic Acids, Sodium Borohydride
ID: J54-Y2008-2440
