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Unusual triethylamine catalyzed rearrangement of bicyclic endoperoxides derived from substituted cycloheptatrienes

✍ Scribed by M.Emin Sengül; Zeynep Ceylan; Metin Balci

Book ID
104207926
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
404 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

Triethylamine catalyzed rearrangement of the substituted bicyclic cycloheptatriene endoperoxides 9,12, 13, 20, 21, 22 and 30 underwent different reaction modes and resulted in the formation of ring contraction products in the case of 9, 10, 12 and 13. However, 20, 21, and 30 provided rearranged diketones 23, 24 and 32 almost in quantitative yield. The mechanism of these reactions was discussed.

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