100790-00-9Relevant academic research and scientific papers
Synthesis of 3-Substituted Aryl[4,5]isothiazoles through an All-Heteroatom Wittig-Equivalent Process
Xu, Fanghui,Chen, Yuan,Fan, Erkang,Sun, Zhihua
, p. 2777 - 2779 (2016)
Extending the previous use of tert-butyl sulfoxide as the sulfinyl source, intramolecular sulfinylation of sulfonamides was successfully performed. The resulting sulfinimides were not isolated and instead were believed to go through an all-heteroatom Witt
Acid-Catalyzed Synthesis of Aryl[4,5]isothiazoles through a Sulfenic Acid Pathway
Sun, Zhihua,Yuan, Hong
, p. 1904 - 1908 (2019)
A new method to efficiently prepare 3-substituted aryl[4,5]isothiazoles by simply heating the starting materials with a catalytic amount of p -toluenesulfonic acid in toluene is reported. This simple procedure is well suitable for a variety of substrates
Chemistry of Sulfenic Acids. 7. Reason for the High Reactivity of Sulfenic Acids. Stabilization by Intramolecular Hydrogen Bonding and Electronegativity Effects
Davis, Franklin A.,Jenkins, Linda A.,Billmers, Robert L.
, p. 1033 - 1040 (2007/10/02)
It is proposed that the reason sulfenic acids (RSOH) are so reactive and usually not isolated or even detected is that they form thiosulfinates (RS(O)SR) so readily.This is a consequence of the sulfenic acid hydrogen-bonded dimer, 1, which lowers the energy of activation for thiosulfinate formation.The stability of the few sulfenic acids that have been isolated can be explained in terms of steric, electronic, and intramolecular hydrogen-bonding effects which prevent dimer formation.The importance of these effects on the stability of simple unstable sulfenic acids was demonstrated by flash vacuum pyrolysis (FVP) and the thiosulfinate/vinyl sulfoxide ratio.A novel, high yield, rearrangement of sulfenic acid 19f to 1,3-benzothiazine 26 was observed.
