Synthesis of adamantane derivatives. LXVIII. Cycloaddition reactions of 2-(1-adamantyl)-1,3-butadiene and -heterodienes.
作者:TADASHI SASAKI、KAZUO SHIMIZU、MASATOMI OHNO
DOI:10.1248/cpb.32.1433
日期:——
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.