Organic Chemistry Portal

Abstracts

Search:

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: snowdenbama.ua.edu

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

DOI: 10.1021/ol8016484 (free Supporting Information)


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



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