Electrostatic vs. Orbital Control of Facial Selectivities in π Systems: Experimental and Theoretical Study of Electrophilic Additions to 7‐Isopropylidenenorbornanes | Zendy

Mehta Goverdhan | Zendy; Khan Faiz Ahmed | Zendy; Gadre Shridhar R. | Zendy; Shirsat Rajendra N. | Zendy; Ganguly Bishwajit | Zendy; Chandrasekhar Jayaraman | Zendy

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Electrostatic vs. Orbital Control of Facial Selectivities in π Systems: Experimental and Theoretical Study of Electrophilic Additions to 7‐Isopropylidenenorbornanes

Author(s) -

Mehta Goverdhan,

Khan Faiz Ahmed,

Gadre Shridhar R.,

Shirsat Rajendra N.,

Ganguly Bishwajit,

Chandrasekhar Jayaraman

Publication year - 1994

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199413901

Subject(s) - substituent , electrophile , ab initio , norbornane , electrophilic addition , computational chemistry , chemistry , derivative (finance) , molecular orbital , medicinal chemistry , stereochemistry , organic chemistry , molecule , catalysis , financial economics , economics

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, COOCH 3 .

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