Acetylenic Sulfinamides: A Novel Class of Compounds

Selling, H. A.; MAK, H. J.

doi:10.1080/00397917608072622

Cited by 14 publications

(2 citation statements)

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“…At the same time the literature concerning the use of heterocumulene such as phenylsulfinylamine in reactions of this type are rather scarce [4][5][6]. An interaction of arenesulfinylamines with lithiated alkynes and organylethynylmagnesium bromides leading to the formation of N-aryl(organylethynyl)sulfinamides has been reported [4,5].…”

Section: Introductionmentioning

confidence: 96%

“…An interaction of arenesulfinylamines with lithiated alkynes and organylethynylmagnesium bromides leading to the formation of N-aryl(organylethynyl)sulfinamides has been reported [4,5]. The use of allenylcopper compounds in the reaction with phenylsulfinylamine affords N-phenyl-2-alkynylsulfinamides, which, upon treatment with either sodium ethoxide in ethanol or butyllithium and subsequent addition of AgBr (LiBr) 3 , undergo cyclization to N-phenyl-2,5-dihydroisothiazole S-oxides [6].…”

Section: Introductionmentioning

confidence: 98%

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Reaction Of Metallated Allenes With Phenylsulfinylamine

et al. 2002

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Lithiated allenes or allenylmagnesium bromides readily react (THF/hexane, À 90 to À 105 C, 10-15 min) with phenylsulfinylamine to give N-phenyl-2-alkynylsulfinamides. The reaction of metallated 3-methylbuta-1,2-diene leads to the formation of not only 2-methyl-N-phenylbut-3-yne-2-sulfinamide, but also its allenic isomer, 3-methyl-N-phenylbuta-1,2-diene-1-sulfinamide. Metallated penta-1,2-diene, 1-propa-1,2-dienylcyclohexane and 4,4-dimethylpenta-1,2-diene react with phenylsulfinylamine to form acetylenes 3, 4 and 6 respectively as a mixture of diastereoisomers.

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