Reactions of silver(I) trifluoromethanethiolate with halotrimethylsilanes: in situ generation of trimethylsilyl trifluoromethyl sulfide

Adams, D. J. , Tavener, S. J. and Clark, J. H. (1998) Reactions of silver(I) trifluoromethanethiolate with halotrimethylsilanes: in situ generation of trimethylsilyl trifluoromethyl sulfide. Journal of Fluorine Chemistry, 90(1), pp. 87-91. (doi: 10.1016/S0022-1139(98)00163-8)

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Abstract

Silver(I) trifluoromethanethiolate reacts with halotrimethylsilanes to produce silver halide, fluorotrimethylsilane and an oligomeric species of formula (CS)3 (SCF3)2. Variable temperature 19F NMR spectroscopy reveals that the reaction proceeds via trimethylsilyl trifluoromethyl sulfide (Me3SiSCF3), which rapidly decomposes on warming. This acts as a source of nucleophilic trifluoromethanethiolate, reacting with highly activated haloaromatics to produce trifluoromethyl aryl sulfides.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Adams, Dave
Authors: Adams, D. J., Tavener, S. J., and Clark, J. H.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Fluorine Chemistry
Publisher:Elsevier
ISSN:0022-1139
ISSN (Online):1873-3328
Published Online:02 March 1999

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