Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 0, 1973
Previous Article Next Article

1.5-Dienes from allylic alcohols and carbonyl compounds by successive Claisen rearrangement, Wittig reaction, and Cope rearrangement: an attempted synthesis of ‘propylure’

Abstract

3,3-Dialkylallyl alcohols and aldehyde dimethyl acetals condense with Claisen rearrangement to form substituted pent-4-enals. The hexa-1,5-dienes made from these aldehydes by the Wittig reaction then rearrange in the opposite direction according to Cope. While this scheme worked very well with n-heptanal dimethyl acetal and 3-methylbut-2-en-1-ol, yielding 2-methyldodeca-2,6-diene, it was less successful when applied to an attempted synthesis of ‘propylure’[(5E)-10-propyltrideca-5,9-dienyl acetate].

Back to tab navigation

Article information


J. Chem. Soc., Perkin Trans. 1, 1973, 2738-2741
Article type
Paper

1.5-Dienes from allylic alcohols and carbonyl compounds by successive Claisen rearrangement, Wittig reaction, and Cope rearrangement: an attempted synthesis of ‘propylure’

R. C. Cookson and N. W. Hughes, J. Chem. Soc., Perkin Trans. 1, 1973, 2738
DOI: 10.1039/P19730002738

Search articles by author

Spotlight

Advertisements