Convenient synthesis and cycloaddition reactions of 2-phenylseleno-1,3-butadiene and 2-trialkylstannyl-1,3-butadienes

Abstract

The facile preparation of 2-trialkylstannyl-1,3-butadienes and 2-phenylseleno-1,3-butadiene by reaction of 2-(1,3-butadienyl)magnesium chloride with trialkylstannyl chlorides and phenylselenium chloride, respectively, is reported. The Diels-Alder reactivity of these dienes with a variety of activated dienophiles is also described. Finally, a novel transmetallation of tin, in vinyl stannanes, to selenium by use of phenylselenium chloride is outlined.