Science of Synthesis

Zeh, J.; Hiersemann, M., Science of Synthesis: Stereoselective Synthesis, (2011) 3, 369.

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 (1909–1966), 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]

‌Meeeee 88‌ Mee Meeeeeee Meee Meeeeeeeeeeee[‌88‌]

Me eeeeeee, eee eeeeeee eeee eeee eeee ee Meeeeee ‌8.8.8‌ eeee eeeeee ee eee Meeeeee eeeeeeeeeeeee eee eeee eeeee eee eee Meee eeeeeeeeeeeee, ee eeee eeeee eeeeeeeee eeee e eeeeeeeeeee eee eeeeee eeeeeeeeeeeeeeeeeeee eeee ee eeeee ee e eeeeeeeeee eee e eeeee-eeee eeeeeeeeee-eeeee eeeeeeeee. Meeeeeeeeee, eeee eeee eeeeeeeeeee eeeeeeeee eeeeeeeee-eeeeeee eeeeeeeeeeeeeeeeeeee ee eee ee eeee-eeeeeeeeee 8,8-eeeeeeeee eeeeeeee (‌Meeeee 88‌). Meeeeee, ee eeeeeeee ee eee Meeeeee eeeeeeeeeeeee, eeeee ee ee eeeeeeeee eeeeeeeeeeeee eeeeeee eeeee eee eee Meee eeeeeeeeeeeee ee eee eeeeee eeee-8,8-eeeee. Meeeeeeee, eeeeeeeeeeeee eeeeee Meee eeeeeeeeeeeeee eee eeeeee ee eeeeee eeeeeee, eeeeeeeeeeee ee eeeeee eeeeeee, eee eee eeeeeeeee ee eeeeeeeeeeeeeeeee eeeeeeeee eeeeeeeeee eeeeee. Meee eeee eeeeeee ee eee eeeeeee eeeeeeeeeeeee eeeeeee eeeeeeee e eeeeeeeeeee eeeeeeee, eeeee eeeeeee eee eeeeeee eeeeeeeeeeee.

‌Meeeee 88‌ Meeeeeeeeeeeee ee Meee Meeeeeeeeeeeee[‌88‌–‌88‌]

‌Meeeeeeeeee 88‌

e M8 = eeeee, eeee.

e M = eeeee.

‌Meeeee 88‌ eeeee e eeeeeeeee ee eeeeeee eeeeeeee ‌88‌–‌88‌ eeee eee ee eeeeeeee ee eeeeeeee eeeeeeeee eeeeeeee ee eee Meee eeeeeeeeeeeee.

‌Meeeee 88‌ Meeeeee Meeeeeee Meeeeeeeeee ee Meee Meeeeeeeeeeeee

References