Intra-and Intermolecular Alkylation of N, O-Acetals and π-Activated Alcohols Catalyzed by in Situ Generated Acid

…, D Bolien, MJ Tranchant, C Taillier, I Jabin…

Index: Hamon, Melanie; Dickinson, Niall; Devineau, Alice; Bolien, David; Tranchant, Marie-Jose; Taillier, Catherine; Jabin, Ivan; Harrowven, David C.; Whitby, Richard J.; Ganesan; Dalla, Vincent Journal of Organic Chemistry, 2014 , vol. 79, # 5 p. 1900 - 1912

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Citation Number: 8

Abstract

Intramolecular and intermolecular alkylations of carbocation precursors of limited ionization ability, principally N, O-acetals, without the use of an exogenous reagent have been developed. The reactions are carried out in 1, 1, 2, 2-tetrachloroethane (TCE) and take advantage of the ability of this solvent to continuously release small amounts of HCl by thermolytic elimination. A study of the reaction led to several improved protocols such as ( ...