Direct Room??Temperature Lactonisation of Alcohols and Ethers onto Amides: An “Amide Strategy” for Synthesis

…, D Petkova, C Madelaine, N Maulide

Index: Valerio, Viviana; Petkova, Desislava; Madelaine, Claire; Maulide, Nuno Chemistry - A European Journal, 2013 , vol. 19, # 8 p. 2606 - 2610

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Citation Number: 31

Abstract

The amide functional group is usually considered as the most robust and resistant of the carboxylic acid derivatives. As taught in standard organic chemistry undergraduate textbooks, the reduced electronegativity of the nitrogen atom in an amide (as compared to oxygen in esters or acids) results in more effective orbital overlap with the adjacent carbonyl, thus markedly reducing its electrophilic character.[1] Therefore, it is not surprising that ...