Dimethyl Sulfoxide as a Synthon in Organic Chemistry

doi:10.1055/s-0035-1560429

Paper

Dimethyl Sulfoxide as a Synthon in Organic Chemistry

Published Mar 10, 2016 · Ebenezer Jones-Mensah, Megha Karki, Jakob Magolan

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Abstract

Abstract Dimethyl sulfoxide is generally characterized as a solvent and oxidant rather than as a substrate, building block, or synthon in organic chemistry. However, an abundance of reports have recently appeared that demonstrate dimethyl sulfoxide acting in these roles. This review article offers a comprehensive summary of the literature on this topic until the end of 2015. Synthetic transformations that have utilized the ‘C–S–C’, ‘C’, and ‘C–S’ fragments of dimethyl sulfoxide as building blocks are systematically summarized. 1 Introduction 2 History and Recent Highlights of DMSO-Based Oxidations 3 DMSO-Based Methylthiomethylation (–CH2SMe) 4 DMSO as a One-Carbon Synthon 4.1 DMSO-Based Methylation (–Me) 4.2 DMSO-Based Methylenation (–CH2–) 4.3 DMSO-Based Annulation/Aromatization (=CH–) 4.4 DMSO-Based Formylation (–CHO) 4.5 DMSO-Based Cyanation (–CN) 5 DMSO as Synthon for ‘S–C’ Functionalities 5.1 DMSO-Based Thiomethylation (–SMe) 5.2 DMSO-Based Methylsulfonylation (–SO2Me) 6 Summary and Conclusions

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Study Snapshot

Dimethyl sulfoxide can act as a substrate, building block, and synthon in organic chemistry, despite its traditional role as a solvent and oxidant.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Dimethyl Sulfoxide as a Synthon in Organic Chemistry

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