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Experimental and Computational Insights into the Water‐Mediated Decomposition of N ‐Sulfonylhydrazones: A Catalyst‐Free Synthesis of γ‐Keto/Nitrile Sulfones
Author(s) -
Goyal Shagun,
Budhiraja Meenakshi,
Mandal Debasish,
Tyagi Vikas
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900728
Subject(s) - chemistry , nitrile , acrylonitrile , sulfonyl , catalysis , reagent , decomposition , base (topology) , combinatorial chemistry , organic chemistry , copolymer , polymer , mathematical analysis , alkyl , mathematics
This work is an example of water‐mediated decomposition of N ‐sulfonylhydrazones used as sulfonyl‐transferring reagents in the selective sulfa‐Michael reaction in the absence of any base or catalyst. A wide range of substituted N ‐sulfonylhydrazones were tested as sources of sulfonyl anions with enones or acrylonitrile, which in turn provided the γ‐ keto/nitrile sulfones in very good yields. Additionally, we have performed a rigorous computational mechanistic study to investigate the role of water which demonstrates the key role of water in the hydrogen abstraction from N ‐tosylhydrazone to initiate the reaction.