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Photochemistry of Chlorinated 2-Cycloalkenones

✍ Scribed by Isabelle Altmeyer; Paul Margaretha

Publisher
John Wiley and Sons
Year
1977
Tongue
German
Weight
400 KB
Volume
60
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The 6‐chloro‐2‐cyclohexenones 3, 6 and 11, and the 5‐chloro‐2‐cyclopentenone 15 were newly synthesized. The results obtained with compounds 3 and 15 in photocycloadditions to olefins show that the oxetane vs. cyclobutane product ratio is reduced by the substitution of florine by chlorine in the α′ ‐position of the enone. No oxetanes are formed in the intramolecular photocycloaddition of 6. Compound 11 does not photoadd to olefins. The newly synthesized 2‐chloro‐3‐cyclohexenones 8 and 9 are also photostable towards light of λ=366 nm, but π‐π*‐excitation (λ=254 nm) in pentane leads to the formation of 4,4‐dimethylcyclohexanone (29).

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