Singlet oxygen additions to hexacyclo[10.2.1.02,11.04,9.04,14.09,13]pentadeca-5,7-dien-3,10-diones. A remarkable substituent effect on p-face selectivity induced by transition state geometric distortions

Mehta, Goverdhan ; Subramanian, Uma R. ; Pramanik, Animesh ; Chandrasekhar, Jayaraman ; Nethaji, Munirathnam (1995) Singlet oxygen additions to hexacyclo[10.2.1.02,11.04,9.04,14.09,13]pentadeca-5,7-dien-3,10-diones. A remarkable substituent effect on p-face selectivity induced by transition state geometric distortions Journal of the Chemical Society, Chemical Communications (6). pp. 677-678. ISSN 0022-4936

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1995...

Related URL: http://dx.doi.org/10.1039/C39950000677

Abstract

Face selectivity in singlet oxygen addition to a rigid polycyclic diene is reversed by sterically neutral 1,4-substitution, an effect attributed to lone pair repulsions induced by out-of-plane bending at the transition state.

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