An unusual example of stereoelectronic control in the ring opening of 3,3-disubstituted 1,2-dichlorocyclopropenes

Mark S. Baird; Juma'a R. Al Dulayymi; Henry S. Rzepa; Vera Thoss

doi:10.1039/C39920001323

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Journal of the Chemical Society, Chemical Communications

Issue 18, 1992

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

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An unusual example of stereoelectronic control in the ring opening of 3,3-disubstituted 1,2-dichlorocyclopropenes

Mark S. Baird, Juma'a R. Al Dulayymi, Henry S. Rzepa and Vera Thoss

J. Chem. Soc., Chem. Commun., 1992, 1323-1325

DOI: 10.1039/C39920001323

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Abstract
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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.

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An unusual example of stereoelectronic control in the ring opening of 3,3-disubstituted 1,2-dichlorocyclopropenes

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Journal of the Chemical Society, Chemical Communications

An unusual example of stereoelectronic control in the ring opening of 3,3-disubstituted 1,2-dichlorocyclopropenes

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