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A Simple Alkylative 1,2-Carbonyl Transposition of Cyclohexenones

✍ Scribed by Wolfgang Oppolzer; Tarun Sarkar; Kumar K. Mahalanabis

Publisher: John Wiley and Sons
Year: 1976
Tongue: German
Weight: 577 KB
Volume: 59
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19760590614

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✦ Synopsis

Abstract

Acid catalysed dehydration of the diols 5, derived from the cyclohexenone 3 affords mixtures of 8 and 11. The product ratio 8/11, although strongly dependent on both the reaction conditions and the substituent R, is independent of the diol configuration; this indicates a cationic intermediate 6. Conditions were found, which allow the sequence A → B → C → D (Scheme 2) to be applied to the syntheses of the enones 8, 21 and 25 in fair to good yields from the corresponding cyclohexenones 3, 18 and 22.

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