Issue 1, 2023
From the journal:

Organic & Biomolecular Chemistry

Synthetic and computational investigation of neighboring group participation by a nucleophilic disulfide bond†

Takuhei Yamamoto, ORCID logo *ab   Koki Fukuta,a   Yuki Kariya,a   Taiki Matsuura,a   Hiroaki Hagiwara, ORCID logo c   Bunji Uno ORCID logo d  and  Yukihiro Esakaab  

* Corresponding authors

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

b United Graduate School of Drug Discovery and Medical Information Science, Gifu University, 1-1 Yanaido, Gifu 501-1194, Japan

c Department of Chemistry, Faculty of Education, Gifu University, 1-1 Yanaido, Gifu 501-1193, Japan

d Faculty of Pharmacy, Gifu University of Medical Science, 4-3-3 Nijigaoka, Kani, Gifu 509-0923, Japan

Abstract

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.

Graphical abstract: Synthetic and computational investigation of neighboring group participation by a nucleophilic disulfide bond

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Article information

DOI
https://doi.org/10.1039/D2OB01574A
Article type
Communication
Submitted
30 Aug 2022
Accepted
18 Nov 2022
First published
18 Nov 2022

Org. Biomol. Chem., 2023,21, 65-68

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

T. Yamamoto, K. Fukuta, Y. Kariya, T. Matsuura, H. Hagiwara, B. Uno and Y. Esaka, Org. Biomol. Chem., 2023, 21, 65 DOI: 10.1039/D2OB01574A

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