An unusual example of stereoelectronic control in the ring opening of 3,3-disubstituted 1,2-dichlorocyclopropenes
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 18,p. 1323-1325
- https://doi.org/10.1039/c39920001323
Abstract
Quantitative SCF-MO calculations at the PM3 and ab initio level reveal that the origin of the stereoselective ring opening of 1,2-dichloro-3,3-disubstituted cyclopropenes (1, R2= CH2Cl, CH2OMe or CH2Ph) to give vinylcarbenes 2via transition state 5 arises from stereoelectronic control, in contrast to that of cyclopropenes having bulky non-polar substituents such as R2= Pri which favours a less hindered transition state 6.Keywords
This publication has 0 references indexed in Scilit: