Medium-sized Cyclophanes. Part 40.1 Generation of a Bis(o-quinone methide) from [n.2]Cyclophanes having a Spiro Skeleton and their Trapping Reaction with Nucleophiles and Dienophiles

Abstract

Spiro compounds 2, obtained from the oxidation of dihydroxy[n.2]metacyclophanes 1 with K ₃ Fe(CN) ₆ , readily generate a bis(o-quinone methide) 3 with mild heating which is trapped with nucleophiles and dienophiles to give diarylalkanes 4–6 and [4+2] cycloadducts 8, respectively.