Origins of the regioselectivity of cyclopropylcarbinyl ring opening reactions in bicyclo [n.1.0] systems

Robert A. Batey; Peter Grice; John D. Harling; William B. Motherwell; Henry S. Rzepa

doi:10.1039/C39920000942

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Journal of the Chemical Society, Chemical Communications

Issue 13, 1992

Journal of the Chemical Society, Chemical Communications was published between 1972 - 1995.

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Origins of the regioselectivity of cyclopropylcarbinyl ring opening reactions in bicyclo [n.1.0] systems

Robert A. Batey, Peter Grice, John D. Harling, William B. Motherwell and Henry S. Rzepa

J. Chem. Soc., Chem. Commun., 1992, 942-944

DOI: 10.1039/C39920000942

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Abstract
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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.

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Robert A. Batey
Peter Grice
John D. Harling
William B. Motherwell
Henry S. Rzepa

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Origins of the regioselectivity of cyclopropylcarbinyl ring opening reactions in bicyclo [n.1.0] systems

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