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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, Email: bkpatelpostmark.net

R. Gopinath, Sk. J. Haque, B. K. Patel, J. Org. Chem., 2002, 67, 5842-5845.

DOI: 10.1021/jo025701o (free Supporting Information)


Abstract

Acyclic and cyclic acetals of various carbonyl compounds were obtained in excellent yields in the presence of trialkyl orthoformate and a catalytic amount of tetrabutylammonium tribromide in absolute alcohol. This convenient, mild, chemoselective method allows acetalization of an aldehyde in the presence of ketone, unsymmetrical acetal formation, and tolerates acid-sensitive protecting groups.

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Key Words

Acetals, Dimethyl Acetals, Diethyl Acetals, 1,3-Dioxolanes, 1,3-Dioxanes


ID: J42-Y2002-910