Synthetic and computational investigation of neighboring group participation by a nucleophilic disulfide bond
ORGANIC & BIOMOLECULAR CHEMISTRY(2022)
摘要
Disulfide bonds of 2-isocyanatophenyl methyl disulfide and 2-endo-isocyanato-6-endo-(methyldisulfanyl)bicyclo[2.2.1]heptane showed neighboring group participation in the formation of thiocarbamates. Natural Bond Orbital (NBO) analyses revealed that the unusual nucleophilicity requires a rigid through-space interaction between a lone pair of the disulfide bond and an antibonding orbital of isocyanate.
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关键词
neighboring group participation,disulfide,bond
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