Tetrabutylammonium Tribromide (TBATB) as An Efficient Generator of HBr for an Efficient Chemoselective Reagent for Acetalization of Carbonyl Compounds†

Rangam Gopinath, Sk. Jiaul Haque, and Bhisma K. Patel*
Department of Chemistry, Indian Institute of Technology, Guwahati-781 039, India bkpatel@postmark.net
J. Org. Chem., 2002, 67 (16), pp 5842–5845
DOI: 10.1021/jo025701o
Publication Date (Web): June 27, 2002
Copyright © 2002 American Chemical Society
†

 Dedicated to professor S. Ranganathan on the occasion of his 68th birthday.

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*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Abstract Image

Acyclic and cyclic acetals of various carbonyl compounds were obtained in excellent yields under a mild reaction condition in the presence of trialkyl orthoformate and a catalytic amount of tetrabutylammonium tribromide (TBATB) in absolute alcohol. Chemoselective acetalization of an aldehyde in the presence of ketone, unsymmetrical acetal formation, shorter reaction times, mild reaction conditions, the stability of acid-sensitive protecting groups, high efficiencies, facile isolation of the desired products, and the catalytic nature of the reagent make the present methodology a practical alternative.

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History

  • Published In Issue August 09, 2002
  • Received March 11, 2002

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