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3.7.2 The Cope Rearrangement and Related Reactions

DOI: 10.1055/sos-SD-203-00213

Zeh, J.; Hiersemann, M.Science of Synthesis: Stereoselective Synthesis, (20113369.

The [3,3]-sigmatropic rearrangement of 1,5-dienes can be considered as an all-carbon variant of the Claisen rearrangement. This type of rearrangement was discovered in 1940 by Arthur C. Cope (19091966), who observed the formation of ethyl 2-cyano-3,4-dimethylhepta-2,6-dienoate upon distillation of ethyl 2-allyl-2-cyano-3-methylpent-3-enoate (Scheme 25).[‌36‌]

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References