Bifunctionalized resins. Applications to the synthesis of insect sex attractants

Abstract

A 2% crosslinked divinylbenzene–styrene copolymer, incorporating benzoyl chloride groups, was used to monoprotect the symmetrical diol 1,10-decanediol. The corresponding monotrityl ether and cis-10-tetradecen-1-ol were prepared by this system, the latter by a Wittig reaction of a polymer-bound ylide with an aldehyde in the solution phase. A series of bifunctionalized resins containing proximally located trityl alcohol and benzoic acid groups was prepared in an attempt to prepare diol linked to the polymer via both a trityl ether and a benzoate linkage. It was established that these polymers bound 1,10-decanediol exclusively at one end only. Polymers, containing both trityl alcohol and benzoic acid groups in a random array or polymers containing proximally located trityl alcohol groups, gave mixtures of both monoprotected and doubly protected diol.