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Sequential Methyl–Fluorine Exchange Reactions of Siloxide Ions in the Gas Phase
Author(s) -
Correra Thiago C.,
Riveros José M.
Publication year - 2012
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.201203970
Subject(s) - fluorine , chemistry , nucleophile , metathesis , gas phase , salt metathesis reaction , ion , reaction mechanism , ion exchange , computational chemistry , organic chemistry , polymerization , catalysis , polymer
Exchange Me for a fluorine : Trimethylsiloxide ions in the presence of NF 3 in the gas phase undergo an unusual and sequential metathesis‐type reaction wherein methyl groups are exchanged for fluorine. Theoretical calculations suggest that the reaction proceeds by a three‐step internal‐nucleophilic‐displacement mechanism which features a pentacoordinated siliconate species (see picture) as a transition state rather than as an intermediate.