1.
Org Lett
; 4(12): 2059-61, 2002 Jun 13.
Article
in English
| MEDLINE
| ID: mdl-12049517
ABSTRACT
[reaction: see text] The H/D exchange of the lactone-fused cycloheptatriene 1 is over 1000 times faster than that of the epimer 2. Interconversion of 1 and 2 provides an equilibrium mixture of 1:0.7, showing a similar stability of the isomers. Protonation of the common enolate 7 occurs far more readily on the more hindered face. Cycloheptatrienide anion is bent and as stable as a divinylcarbanion.