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2-Alkynylcyclopent-2-enols from 2-Alkynylcyclohex-2-enones via 1-Alkynyl-7-oxabicyclo[4.1.0]heptan-2-ones

✍ Scribed by Birgit Sander; Sven Andresen; Stefan Reichow; Katia Dubois; William C. Agosta; Paul Margaretha

Publisher
John Wiley and Sons
Year
1996
Tongue
German
Weight
404 KB
Volume
79
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

2‐Alkynylcyclohex‐2‐enones 1a–c and 2a–c react with H~2~O~2~/NaOH in MeOH to afford 1‐alkynyl‐7‐oxabicyclo[4.1.0]heptan‐2‐ones 3a–c and 4a–c, respectively. The 3‐unsubstituted bicyclic epoxy ketones 3a, 3b, and 4a, 4b react further with H~2~O~2~/NaOH, undergoing ring contraction and (formal) decarbonylation to give 2‐alkynylcy‐clopent‐2‐enols 5a, 5b, and 6a, 6b, respectively. Epoxy ketones 3 are also obtained under neutral conditions on irradiation (λ = 350 nm) of cyclohexenones 1 in air‐saturated benzene solution. Similarly, under neutral conditions oxo‐cycloalkenecarbonitriles 8 react (thermally) with H~2~O~2~ in MeCN to give the oxabicyclic carbonitriles 9.

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