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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.