Issue 0, 1973
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Sequential Claisen and Cope rearrangements: the propenyl ether and acetate of 3-methylhept-6-en-1-yn-3-ol

Bruce Bowden,   Richard C. Cookson  and  Harry A. Davis  

Abstract

The synthetic potential of a Claisen followed by a Cope rearrangement is illustrated by the reactions of 3-methylhept-6-en-1-yn-3-ol (II). This propargylic alcohol (II) condenses with methyl isopropenyl ether with Claisen rearrangement to give 6-methyldeca-4,5,9-trien-2-one (IV), which isomerises in boiling xylene through the product of Cope rearrangement (V) to 5-isopropylideneocta-trans-3,7-dien-2-one (VI). The acetate (IX) of the alcohol (II) undergoes an analogous series of rearrangements to the allenyl acetate (X) and the dienyl acetate (XII).

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Article information

DOI
https://doi.org/10.1039/P19730002634
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1973, 2634-2637

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Sequential Claisen and Cope rearrangements: the propenyl ether and acetate of 3-methylhept-6-en-1-yn-3-ol

B. Bowden, R. C. Cookson and H. A. Davis, J. Chem. Soc., Perkin Trans. 1, 1973, 2634 DOI: 10.1039/P19730002634

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