312909-09-4Relevant articles and documents
Reaction of dimethoxycarbene with strained cyclic carbonyl compounds
Venneri,Warkentin
, p. 1194 - 1203 (2000)
A cyclopropanone, a cyclopropenone, cyclobutanones, a cyclobutane-1,3-dione, and a cyclobutene-1,2-dione reacted with dimethoxycarbene to afford acetals of the next larger ring by formal insertion of the carbene into a C-C bond α to the carbonyl group. When either of two saturated α-ring carbons could be involved in the process, the ring expansion was selective, affording primarily the product of apparent insertion into the more substituted ring bond. With 2,3-dimethoxycyclobutene-1,2-dione, insertion occurred between the carbonyl groups and with β-propiolactone it occurred at the lactone bond. β-Propiolactam, however, reacted by insertion of the carbene into the N-H bond.
