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A convenient preparation of N- (arenesulfonyl) sulfoximines by oxidation of N- (arenesulfonyl) sulfilimines with sodium hypochlorite in a two phase system

โœ Scribed by Naomichi Furukawa; Kunihiko Akutagawa; Toshiaki Yoshimura; Shigeru Oae


Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
215 KB
Volume
22
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


Sulfoximines are attractive organic sulfur compounds as alkylidene or chiral transfer reagent like sulfur ylides. 1) For example, Johnson et al. revealed that cc-sodio derivatives of N-(arenesulfonyl)sulfoximines are useful nucleophilic alkylidene transfer reagents, e.g., for the conversion of aldehydes and ketones to the corresponding oxiranes. 2) As to synthetic procedures for N-(arenesulfonyl)sulfoximines following several methods have been exploited, namely, oxidations of sulfilimines, 3) oxidative iminations of sulfoxides, 2,4) formations of sulfur-carbon linkages of sulfoximines 5) and sulfonylations of N-H sulfoximines. 6) However, except for sulfonylation of N-H sulfoximines, these methods have only limited uses to prepare N-sulfonyl S,S-dialkyl and S-alkyl S-aryl sulfoximines. Only the other route to prepare S,S-diary1 N-(arenesulfonyl)sulfoximines involves treating arenesulfonylchlorides with the corresponding N-H sulfoximines which are prepared by oxidation of N-H sulfilimines 5) with potassium permanganate, 7) sodium metaperiodate8) or m-chloroperbenzoic acid, 6) however this procedure needs several steps. Recently, Swern') and Johnson3) reported that oxidation of S,S diphenyl N-(p-tolylsulfonyl)sulfilimine with m-chloroperbenzoate anion or perhydroxy anion generated .in A.ih in basic aqueous alcoholic media affords the corresponding sulfoximine


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