Friedel-crafts reactions of bis (trimethylsilyl) polyynes with acyl chlorides; a useful route to terminal-alkynyl ketones

DRM Walton, F Waugh

Index: Walton,D.R.M.; Waugh,F. Journal of Organometallic Chemistry, 1972 , vol. 37, p. 45 - 56

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Citation Number: 160

Abstract

Abstract Bis (trimethylsilyl) acetylenes, Me 3 Si (C C) n SiMe 3, react with acyl chloride- aluminium chloride complexes, XC 6 H 4 COCl· AlCl 3 in methylene chloride at 0–20 to form the corresponding ketones XC 6 H 4 CO (C C) n SiMe 3 in excellent (n= 1) or moderate (n= 2, 4) yield. Treatment of the products with aqueous methanolic borax results in virtually quantitative liberation of the terminal alkynyl ketones XC 6 H 4 CO (C C) n H. The ...