Organoboron compounds—LXXVII. Polymerization of dibutyl vinylboronate

Abstract

DIBUTYL vinylboronate was synthesized simultaneously by Mikhailov and Tutorskaya [1] and Normant and Braun [2] in 1959. The latter authors noted that derivatives of vinylboronic acid are capable of spontaneous polymerization but they did not s tudy the polymerization conditions or the properties of the polymers. There is some information in the literature on the polymerization of certain other unsaturated organoboron compounds. For example Mikhailov and Tutorskaya [3] reported that allylboronic anhydride polymerizes on slow distillation. In another paper [4] the same authors discussed the preparation and properties of a polymer formed b y heating triallylboron with triisobutylboron. The preparation of polymers and copolymers of p-vinylphenylboronic acid and its esters was described by Letsinger and Hamilton [5] and quite recently by Lennarz and Snyder [6]. During a s tudy of some of the reactions of dibutyl vinylboronate, the results of which will be published later, the ester occasionally polymerized spontaneously. In order to investigate the properties of these polymers dibutyl vinylboronate was polymerized by the action of dry air at room temperature and iu bulk in the presence of a,a'-azo-bis-isobutyronitrile.