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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Reactions of 1-Oxaspiro[2.5]octa-5,7-dien-4-ones with nucleophiles

P Cacioli and JA Reiss

Australian Journal of Chemistry 37(12) 2525 - 2535
Published: 1984

Abstract

The 1-oxaspiro[2.5]octa-5,7-dien-4-ones (6-spiroepoxy-2,4-cyclohexadienones) (7) on reaction with a number of carbon, nitrogen, oxygen and halogen nucleophiles produced a variety of interesting substitution and rearrangement products (8)-(19) in moderate yields. The products derived almost exclusively from initial attack of the nucleophile with either the secondary or quaternary carbon of the epoxy ring and these various modes of reaction of the spirocyclic system are discussed. The formation of ortho-substituted phenols from the 1-oxaspiro[2.5]octa-5,7-dien-4-ones suggests that the latter structures may be regarded as polarity-reversed masked phenols. Tropolones, products of a possible ring-expansion reaction, were not observed in any of the reactions investigated.

https://doi.org/10.1071/CH9842525

© CSIRO 1984

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