A New Reaction Pathway in Organophosphorus Chemistry: Competing S N 2 and AE′ Pathways for Nucleophilic Attack at a Phosphorus–Carbon Cage Compound | Zendy

Fish Cheryl | Zendy; Green Michael | Zendy; Kilby Richard J. | Zendy; Lynam Jason M. | Zendy; McGrady John E. | Zendy; Pantazis Dimitrios A. | Zendy; Russell Christopher A. | Zendy; Whitwood Adrian C. | Zendy; Willans Charlotte E. | Zendy

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A New Reaction Pathway in Organophosphorus Chemistry: Competing S N 2 and AE′ Pathways for Nucleophilic Attack at a Phosphorus–Carbon Cage Compound

Author(s) -

Fish Cheryl,

Green Michael,

Kilby Richard J.,

Lynam Jason M.,

McGrady John E.,

Pantazis Dimitrios A.,

Russell Christopher A.,

Whitwood Adrian C.,

Willans Charlotte E.

Publication year - 2006

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200504546

Subject(s) - sn2 reaction , chemistry , nucleophilic substitution , phosphorus , nucleophile , carbon fibers , chloride , cage , competition (biology) , substitution reaction , ion , stereochemistry , medicinal chemistry , organic chemistry , catalysis , materials science , mathematics , combinatorics , composite number , composite material , ecology , biology

Competition : A combination of 31 P NMR spectroscopic and calculational studies have shown that nucleophilic substitution in the phosphorus–carbon cage compound ClP 3 (C t Bu) 2 occurs through competing S N 2‐ and AE′‐type reaction pathways (see scheme for model compound ClP 3 (CH) 2 ). The AE′ mechanism results in the formation of a C 2 v ‐symmetric intermediate prior to release of the chloride ion.

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