Site-selective Diels-Alder reactions of 1, 4, 5, 8-naphthodiquinones with anthracenes and successively with cyclopentadiene: electronic effects vs. steric effects

K Hayakawa, M Aso, K Kanematsu

Index: Hayakawa, Kenji; Aso, Mariko; Kanematsu, Ken Journal of Organic Chemistry, 1985 , vol. 50, # 12 p. 2036 - 2040

Full Text: HTML

Citation Number: 12

Abstract

The cycloaddition reactions of naphthodiquinones with anthracene derivatives have been investigated. While anthracene (4) reacted with naphthodiquinones (1, 2, and 13) at the internal double bond to give the internal adducts (6, 7, and 14), the reaction of 9, lO- substituted anthracenes (5) took place at the terminal double bond to afford the terminal adducts (8, 9, and 15). The successive reaction of adducts 6 and 7 with cyclopentadiene ...