November 1, 1971Journal of the American Chemical Society
Reactions of organolithiums with arylsulfonium salts
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Discussion
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Implication
Experimental study demonstrates nucleophilic substitution pathways between organolithiums and arylsulfonium salts, indicating the formation of transient sulfurane intermediates.
Key Points
- To elucidate the chemical mechanisms and product distributions when organolithium reagents react with various arylsulfonium salts.
- Treated diverse arylsulfonium salts with alkyl- and aryllithium reagents under controlled synthetic conditions.
- Isolated and characterized product mixtures to trace ligand exchange, coupling, and elimination mechanisms.
- Demonstrated that nucleophilic attack of organolithiums on arylsulfonium centers proceeds through tetravalent sulfurane intermediates.
- Identified competitive ligand exchange and carbon–carbon bond coupling pathways governing overall product selectivity.
Cite This Study
LaRochelle et al. (1971) studied this question.