Synthesis of Adamantane Derivatives. LXVIII. Cycloaddition Reactions of 2-(1-Adamantyl)-1, 3-butadiene and-heterodienes

Abstract

2-(1-Adamantyl)-1, 3-butadiene (1) was prepared by p-toluenesulfonic acid-catalyzed dehydration of the corresponding allyl alcohol 5. The Diels-Alder reactions of 1 with a variety of dienophiles proceeded smoothly to give adamantane-substituted six-membered carbo-and heterocycles. Similarly, [4+2] cycloaddition reactions of adamantane-bearing heterodienes afforded some adamantyl-oxazines.