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On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes
Published on: August 5, 2016
Adventures in sulfur-nitrogen chemistry
1Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
The Journal of Organic Chemistry
|November 18, 2006
Summary
This review details 37 years of research on sulfur-nitrogen compounds, focusing on sulfinimines and N-sulfonyloxaziridines. These compounds are valuable for synthesizing chiral building blocks and nitrogen heterocycles.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Heterocyclic Chemistry
Background:
- Sulfur-nitrogen compounds, particularly sulfenamides, were poorly understood.
- Early research focused on sulfenamide thermal properties.
Purpose of the Study:
- To review 37 years of research on sulfur-nitrogen compounds.
- To highlight the synthetic utility of sulfinimines and N-sulfonyloxaziridines.
Main Methods:
- Development of the silver-assisted method for sulfenimine synthesis.
- Selective oxidation of sulfenimines to sulfinimines and N-sulfonyloxaziridines.
- Utilizing enantiomerically pure reagents for asymmetric synthesis.
Main Results:
- N-sulfonyloxaziridines identified as novel aprotic neutral oxidizing reagents.
- High enantioselectivity (ee) achieved in oxidation of enolates and sulfides/selenides.
- Sulfinimines enable versatile asymmetric synthesis of C-N stereocenters.
- Sulfinimine-derived building blocks provide access to diverse nitrogen heterocycles.
Conclusions:
- Sulfur-nitrogen chemistry has advanced significantly over 37 years.
- Sulfinimines and N-sulfonyloxaziridines are powerful tools in modern organic synthesis.
- These compounds are crucial for constructing biologically active molecules and complex heterocycles.
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