Tetrahedron

Rearrangement of the carbon skeleton in the intramolecular photoadduct of anthracene and benzene rings

D Cao, S Dobis, D Schollmeyer, H Meier

Index: Cao, Derong; Dobis, Silvia; Schollmeyer, Dieter; Meier, Herbert Tetrahedron, 2003 , vol. 59, # 28 p. 5323 - 5327

Full Text: HTML

Citation Number: 9

Abstract

The effectivity of optical switching between anthracene derivatives 3a, b and their intramolecular photocycloadducts 4a, b is impaired by traces of acid. The systematic treatment of 4a, b with an increasing excess of formic acid revealed that—apart from the normal enolether cleavage 4a, b→ 6a, b→ 7a, b—a cleavage with rearrangement of the carbon skeleton can occur: 5b→ 6b′. The driving force is a stability enhancement of the ...