Base treatment of benzylic selenonium salts. [2,3] Sigmatropic rearrangements vs. nucleophilic displacement
Abstract
Treatment of certain benzylic selenonium salts with a variety of bases resulted in nucleophilic attack to yield either an alkylation or a benzylation of the base, while the use of sodium amide in liquid ammonia as base generated a selenonium ylide which gave ortho substitution of the benzyl group via[2,3]sigmatropic rerrangement.