Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 125, Issue 18, Pages 5388-5392Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja0298489
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The denticity (O, S-, and C-nucleophilic reactivity) of the dimethylsulfinyl carbanion (dimsyl) toward 1,3,5-trinitrobenzene (TNB) has been studied by NMR spectroscopy, and structures of adducts have been assigned. Three dimsyl adducts are observed for the first time and have been ascribed to the O-adduct 15, the S-adduct 16, and the C-adduct 17. The kinetic (15 > 16 > 17) and thermodynamic preference (17 > 16 > 15) for the reactivity of dimsyl toward TNB is compared to the known O- and C-reactivity of enolate anions and the O- and S-reactivity of dimethyl sulfoxide. Thus, dimsyl apparently represents a unique system in which three adjacent atoms having unshared electron pairs can utilize these in covalent bond formation.
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