Seven-membered ring annulation and spiro-annulation processes via preparation and thermal rearrangement of β-(2-vinylcyclopropyl) α, β-unsaturated ketones

E Piers, HE Morton, I Nagakura…

Index: Piers, Edward; Morton, Howard E.; Nagakura, Isao; Thies, Richard W. Canadian Journal of Chemistry, 1983 , vol. 61, p. 1226 - 1238

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Citation Number: 18

Abstract

Treatment of the β-iodo enones 4 and 26-28 with lithium (phenylthio)(2-vinylcyclopropyl) cuprate (21, mixture of epimers), followed by thermolysis (180° C, 30-45 min) of the initially formed β-(2-vinylcyclopropyl) enones, provided excellent yields of the seven-membered ring annulation products 25 and 30-32, respectively. In similar fashion, the (E)-2-(iodomethylene) cycloalkanones 8 and 29 were transformed efficiently into the spiro-annulation products ...

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