73116-75-3Relevant academic research and scientific papers
One-Pot Sulfoxide Synthesis Exploiting a Sulfinyl-Dication Equivalent Generated from a DABSO/Trimethylsilyl Chloride Sequence
Lenstra, Danny C.,Vedovato, Vincent,Ferrer Flegeau, Emmanuel,Maydom, Jonathan,Willis, Michael C.
supporting information, p. 2086 - 2089 (2016/06/01)
A one-pot process for the synthesis of unsymmetrical sulfoxides using organometallic nucleophiles is described. Sulfur dioxide, delivered from the surrogate DABSO (DABCO-bis(sulfur dioxide)), acts as the initial electrophile and combines with the first organometallic reagent to generate a sulfinate intermediate. In situ conversion of the sulfinate to a sulfinate silyl ester, using TMS-Cl (trimethylsilyl chloride), generates a second electrophile, allowing addition of a second organometallic reagent. Organolithium or Grignard reagents can be employed, delivering sulfoxides in good to excellent yields.
Chemical synthons and intermediates
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Sheet 2, (2008/06/13)
The invention provides novel six and seven-carbon termini-differentiated polypropionate stereotetrads and stereopentads useful in syntheses of natural products. The invention also provides a novel alkylative sulfenylation-desulfonylation process that efficiently transforms enantiopure epoxyvinyl sulfones to syn and anti dienylsulfides in two operations.
Chemistry of Sulfenic Acids. 1. Synthesis of Trimethylsilyl Arenesulfenates (Arenesulfenic Acids)
Davis, Franklin A.,Rizvi, Syed Q. A.,Ardecky, Robert,Gosciniak, Donald J.,Friedman, Arthur J.,Yocklovich, Steven G.
, p. 1650 - 1653 (2007/10/02)
Trimethylsilyl arenesulfenates (5), masked sulfenic acids, are prepared in low yield by trapping the intermediate arenesulfenic acid generated by thermolysis of the corresponding N-benzylidenarenesulfinamide (4) with chlorotrimethylsilane-hexamethyldisilazane.Attempts to prepare 5 by oxidation of trialkyl(phenylthio)silanes (8) with 2-(benzenesulfonyl)-3-phenyloxaziridine (11), an aprotic oxidizing reagent, gave instead the previously unknown trialkylsilyl benzenesulfinates (12).These results are attributed to the enhabced nucleophilicity (α effect) of the intermediate trialkylsilyl arenesulfenate ester.
