Diene-transmissive Diels-Alder Reaction Using 2-Ethoxy-3-methylene-1,4-pentadiene and 2-(2-Bromo-1-ethoxyethyl)1,3-butadiene

Abstract

Abstract A new cross-conjugated triene, 2-ethoxy-3-methylene-1,4-pentadiene, and a triene equivalent, 2-(2-bromo-1-ethoxyethyl)-1,3-butadiene, have been synthesized and their diene-transmissive Diels-Alder cycloadditions are investigated. The initial Diels-Alder reaction selectively occurs not across the diene part substituted with the alkoxyl moiety but the monosubstituted diene. Some cross types of diene-transmissive Diels-Alder reaction are demonstrated using the triene equivalent and two different dienophiles.