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Employing Pressurized Hot Water Extraction PHWE to Explore Natural Products Chemistry in the Undergraduate Laboratory

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Published on: November 7, 2018

Phosphite Esters: Reagents for Exploring S-Nitrosothiol Chemistry.

Chunrong Liu^1,2, Chung-Min Park^2,3, Difei Wang⁴

¹Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Chemical Biology Center, College of Chemistry, and International Joint Research Center for Intelligent Biosensing Technology and Health , Central China Normal University , Wuhan 430079 , Hubei , China.

Organic Letters

|December 7, 2018

Summary

Reactions between S-nitrosothiols and phosphite esters yield thiophosphoramidates and phosphorothioates. Product formation varies based on S-nitrosothiol structure under mild conditions.

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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

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Published on: October 30, 2018

Area of Science:

Organic Chemistry
Organophosphorus Chemistry

Background:

S-nitrosothiols are versatile reagents in organic synthesis.
Phosphite esters are widely used in various chemical transformations.

Purpose of the Study:

To investigate the reactivity of S-nitrosothiols with phosphite esters.
To elucidate the factors influencing the formation of different conjugated adducts.

Main Methods:

Reaction of S-nitrosothiols with triphenyl phosphite, tributyl phosphite, and triethyl phosphite.
Structural analysis of the resulting thiophosphoramidates and phosphorothioates.
Mechanistic studies employing experimental and computational methods.

Main Results:

Two distinct classes of conjugated adducts, thiophosphoramidates and phosphorothioates, were identified.
The regioselectivity of adduct formation was found to be dependent on the steric and electronic properties of the S-nitrosothiol substrate (primary vs. tertiary).
The reactions proceeded efficiently under mild reaction conditions.

Conclusions:

The reaction provides a novel route to thiophosphoramidates and phosphorothioates.
Understanding the reaction mechanism allows for controlled synthesis of specific adducts.
This study expands the synthetic utility of S-nitrosothiols in organophosphorus chemistry.