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Synthetic and computational investigation of neighboring group participation by a nucleophilic disulfide bond. | LitMetric
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Synthetic and computational investigation of neighboring group participation by a nucleophilic disulfide bond.

Takuhei Yamamoto Koki Fukuta Yuki Kariya Taiki Matsuura Hiroaki Hagiwara Bunji Uno Yukihiro Esaka

Org Biomol Chem

Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan.

Published: December 2022

Disulfide bonds of 2-isocyanatophenyl methyl disulfide and 2--isocyanato-6--(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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 Source
http://dx.doi.org/10.1039/d2ob01574aDOI Listing

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