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Phosphite Esters: Reagents for Exploring S-Nitrosothiol Chemistry.

ABSTRACT: The reactions between S-nitrosothiols and phosphite esters, including P(OPh)3, P(OBn)3, and P(OEt)3, were studied. Two different conjugated adducts, thiophosphoramidates and phosphorothioates, were formed, depending on the structures of the S-nitrosothiol substrate (e.g., primary vs tertiary). These reactions proceeded under mild conditions, and the reaction mechanisms were studied using experiments and calculations.

SUBMITTER: Liu C

PROVIDER: S-EPMC6465146 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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Phosphite Esters: Reagents for Exploring S-Nitrosothiol Chemistry.

Liu Chunrong C Park Chung-Min CM Wang Difei D Xian Ming M

Organic letters 20181206 24

The reactions between S-nitrosothiols and phosphite esters, including P(OPh)3, P(OBn)3, and P(OEt)3, were studied. Two different conjugated adducts, thiophosphoramidates and phosphorothioates, were formed, depending on the structures of the S-nitrosothiol substrate (e.g., primary vs tertiary). These reactions proceeded under mild conditions, and the reaction mechanisms were studied using experiments and calculations. ...[more]

PMID: 30520644

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