Origins of the regioselectivity of cyclopropylcarbinyl ring opening reactions in bicyclo [n.1.0] systems
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 13,p. 942-944
- https://doi.org/10.1039/c39920000942
Abstract
Addition of ·CCl3 radicals to sabinene 1(R1= Pri) and a related bicyclo [4.1.0] derivative in BrCCl3 results in kinetic trapping of the exo ring opened intermediate but in CCl4 as solvent the major products are derived from the thermodynamically more stable endo radical; the radical and cationic regioselectivities are related to the features of a PM3 SCF-Mo orbital correlation diagram.Keywords
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