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The Photocyclodimers of 2,3-Dihydro-2,2-dimethyl-4H-pyran-4-one

✍ Scribed by Kerstin Schmidt; Jürgen Kopf; Paul Margaretha

Publisher
John Wiley and Sons
Year
2006
Tongue
German
Weight
66 KB
Volume
89
Category
Article
ISSN
0018-019X

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✦ Synopsis

Dedicated to Professor Heinz Heimgartner on the occasion of his 65th birthday On irradiation (350 nm) in benzene solution, dihydropyranone 3 affords predominantly (75%) the cis-anti-cis HH-dimer 4, but in smaller amounts (12%) also dimer 5, wherein one of the six-membered rings is trans-fused to the (central) cyclobutane ring. The constitution and configuration of 5 was fully elucidated by NMR-analysis. On contact with SiO 2 , 5 isomerizes quantitatively to the cis-anti-cis HTdimer 7, the structure of which was established by X-ray crystal-structure determination.

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