Electrostatic vs. Orbital control of facial selectivities in p systems: experimental and theoretical study of electrophilic additions to 7-isopropylidenenorbornanes

Mehta, Goverdhan ; Khan, Faiz Ahmed ; Gadre, Shridhar R. ; Shirsat, Rajendra N. ; Ganguly, Bishwajit ; Chandrasekhar, Jayaraman (1994) Electrostatic vs. Orbital control of facial selectivities in p systems: experimental and theoretical study of electrophilic additions to 7-isopropylidenenorbornanes Angewandte Chemie International Edition, 33 (13). pp. 1390-1392. ISSN 1433-7851

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/anie.19...

Related URL: http://dx.doi.org/10.1002/anie.199413901

Abstract

Predominantly orbital effects determine the pre ferred syn attack of electrophiles on the norbornane derivative 1 bearing an electron-withdrawing endo substituent. This finding is the result of topological analyses of the electrostatic potentials from ab initio calculations and a comparison of the energies of the transition states calculated with semiempirical methods. R = CN, COOCH3.

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