0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
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]

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[‌88‌‌88‌]

Meeeeeeeeee 88

Me Me Meeeeee Mee
M M, eeeee, eeee Meee [‌88‌]
M MM eee-Meee [‌88‌]
M MM eeeeeee eee-Meee [‌88‌]
M M, eeeee, eeee 8-eeeeee-Meee [‌88‌]
MM8 M, eeeee, eeee 8-eeeeee-Meee [‌88‌]

e M8=eeeee, eeee.

e M=eeeee.

Meeeee 88 eeeee e eeeeeeeee ee eeeeeee eeeeeeee 8888 eeee eee ee eeeeeeee ee eeeeeeee eeeeeeeee eeeeeeee ee eee Meee eeeeeeeeeeeee.

Meeeee 88 Meeeeee Meeeeeee Meeeeeeeeee ee Meee Meeeeeeeeeeeee