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Reaction of 13‐Vertex Carboranes with Nucleophiles: Unprecedented Cage‐Carbon Extrusion and Formation of Monocarba‐ closo ‐dodecaborate Anions
Author(s) -
Zhang Jian,
Chan HoiShan,
Xie Zuowei
Publication year - 2008
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.200804249
Subject(s) - nucleophile , icosahedral symmetry , chemistry , cluster (spacecraft) , carbon fibers , carborane , carbon atom , vertex (graph theory) , bond cleavage , cage , crystallography , hydrogen , stereochemistry , organic chemistry , materials science , combinatorics , catalysis , graph , alkyl , mathematics , composite number , computer science , composite material , programming language
In contrast to icosahedral carboranes , instead of deboration, 13‐vertex carboranes undergo cage‐carbon extrusion and cluster contraction to give icosahedral monocarborane anions on reaction with nucleophiles. In the proposed mechanism, nucleophilic attack on a cage carbon atom cleaves the C cage C cage bond, new C cage B bonds form to preserve cluster integrity, and hydrogen migration generates the final icosahedral product (see scheme).