Electrophilic additions to a 2-methylenebicyclo[2.1.1]hexane system: probing pi-face selectivity for electrostatic and orbital effects |
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| Authors: | Mehta Goverdhan Singh S Robindro Balanarayan P Gadre Shridhar R |
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| Institution: | Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India. gm@orgchem.iisc.ernet.in |
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| Abstract: | reaction: see text] 5-exo-Bicyclo2.1.1]hexane derivatives with remote electron-withdrawing substituents exhibit very modest face selectivity during electrophilic additions due to interplay of several electronic factors. These experimental results have been probed through ab initio MESP maps, bond density calculations, and energetics involved in pre-reaction complexation. |
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