Issue 17, 1976
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

The lithium enolate of cyclo-octa-2,4,6-trienone and its reactions with electrophiles

Penelope A. Chaloner  and  Andrew B. Holmes  

Abstract

Lithium di-isopropylamide catalysed rearrangement of 7,8-epoxycyclo-octa-1,3,5-triene at low temperature gives the lithium enolate of cyclo-octa-2,4,6-trienone, which can be alkylated at C-8 with reactive electrophiles such as methyl iodide, allyl bromide, ethyl iodide, benzyl iodide, and benzeneselenenyl bromide. Bromination of the enolate also occurs at C-8, but reagents such as acetyl chloride and ethyl chloroformate yield only the products of O-acylation.

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Article information

DOI
https://doi.org/10.1039/P19760001838
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1976, 1838-1842

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The lithium enolate of cyclo-octa-2,4,6-trienone and its reactions with electrophiles

P. A. Chaloner and A. B. Holmes, J. Chem. Soc., Perkin Trans. 1, 1976, 1838 DOI: 10.1039/P19760001838

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