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Synthesis 1993; 1993(5): 468-470
DOI: 10.1055/s-1993-25882
short paper
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A New and Efficient Method for the Generation of Sulfene (Thioformaldehyde Dioxide)

Dipak Prajapati* , Satyendra P. Singh, Asha R. Mahajan, Jagir S. Sandhu
  • *Division of Drugs and Pharmaceutical Chemistry, Regional Research Laboratory, Jorhat 785006, India
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Publication Date:
17 September 2002 (online)

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Chlorosulfonylmethylene(dimethyl)ammonium chloride (1) is a highly reactive dehydrating agent which provides an efficient entry to 3, 4-dihydro-3-phenyl-2H-benzothiazine 1,1-dioxides 4, 4, 5-dihydro-4-(4-oxo-4H-1-benzopyran-3-yl)-3H-1,2, 5-benzoxathiazepine 2,2-dioxides 6 and 2-aryl-5-dimethylamino-5, 6-dihydro-2H-1,2,4-thiadiazine 1,1-dioxides 8 via cycloaddition reactions of imines 3, nitrones 5 and 1,3-diazabutadiene derivatives 7 with in situ generated sulfene directly from the corresponding sulfonic acids. The seven-membered azasultone structural assignments are supported by spectroscopic data.