REACTIONS OF ACYL TRIBUTYLPHOSPHONIUM CHLORIDES AND DIALKYL ACYLPHOSPHONATES WITH GRIGNARD AND ORGANOLITHIUM REAGENTS

Ketones and esters (4) were effectively prepared by reaction of Grigna rd reagents with acyl tributylphosphonium chlorides (2), diethyl acylp hosphonates (5), or diisopropyl acylphosphonate (6) derived from acid chlorides and chloroformates (1). Although by the method with 2, 4 is prepared in one-pot operation from 1 and generally in a higher yield, the method with 5 or 6 proved to compensate for the synthesis of 4 wit h 2 in some respects. The readivities of 2, 5, and 6 as electrophiles were also evaluated by comparing their reduction potentials with those of acid chlorides. (C) 1998 Elsevier Science Ltd. All rights reserved .