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

✍ Scribed by Derong Cao; Silvia Dobis; Dieter Schollmeyer; Herbert Meier

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
194 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis

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 0 . The driving force is a stability enhancement of the involved carbenium ions 5b!5b 0 . A further increased excess of formic acid leads finally to a competitive ether cleavage in the tetrahydrofuran ring 5b!8.

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