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A facile synthesis of functionalized cyclopentadienone epoxides by flash thermolytic cycloreversion of tricyclopecenones

✍ Scribed by A.J.H. Klunder; W. Bos; J.M.M. Verlaak; B. Zwanenburg

Book ID
104244154
Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
247 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

A practical synthesis of cyclopentadienone epoxides 10 and their dimethyl acetals 12 by thermal cycloreversion of appropriate tricyclo~5.2~1.02~6~decenone epoxides is de;cribed. Cyclopentadienone epoxides are elusive structures which have mainly been postulatedastransient intermediates in the photochemical transformation of 4-pyrones to 2-pyronesl.Although aryl substituted derivatives are known since 1937', the parent compound 1 (R=H) has been synthesized only very recently whereas no practical synthesis to aliphatically substituted and functionaiized cyclopentadienone epoxides 1 are known yet. Chapman and Hess3 obtained the parent cyclopenta. dienone epoxide by thermal fragmentation of the tetracyclic structure 2 which formally can be COzMe

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