- THERMOLYSES AND REACTIONS WITH NUCLEOPHILES OF N-SULFUR-GROUP-SUBSTITUTED SULFOXIMINES
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Thermolyses and reactions with nucleophiles of S,S-diphenylsulfoximines (1) bearing the following N-sulfur-substituents, i.e., N-p-tolylthio-(b), N-p-tolylsulfinyl-(c), N-(N'-p-tolylsulfonyl-p-toluenesulfinimidoyl)-(d), N-(S',S'-diphenylsulfonio)-(e), N-p-tolylsulfonyl-(f), and N-(N'-p-tolylsulfonyl-p-toluenesulfonimidoyl)-(g), have been examined.The former three sulfoximines (1b-d) are thermally unstable and readily decompose to form diphenyl sulfoxide and diphenyl sulfide by the initial cleavage of the S-N linkage in the original sulfoximines.The latter three sulfoximines (1e-g) fairly stable thermally. 1b-d were found to react with several nucleophiles to afford the corresponding sulfenylated, sulfinylated or sulfinimidoylated products together with N-unsubstituted sulfoximine(1a). 1e was found to react with potassium hydroxide/methanol or chloramine-T/N,N-dimethylformamide to afford diphenyl sulfoxide or S,S-diphenyl-(N-p-tolylsulphonyl)sulfilimine along with 1a in good yields.The latter two sulfoximines (1f,g) were found to be inert in the treatment with a few nucleophiles.S,S-Diphenyl-(N-p-tolylthio)-(1b), -(N-p-tolylsulfinyl)-(1c), -(N-p-toluenesulfinimidoyl)-(1d), and -N-(diphenylsulfonio)-(1e) sulfoximines are all new to sulfoximine chemistry and their chemical behavior and reactivity have not been explored.As a preliminary step, thermal decompositions and reactions of these sulfoximines with several nucleophiles have been examined.
- Oae, Shigeru,Akutagawa, Kunihiko,Furukawa, Naomichi
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p. 223 - 234
(2007/10/02)
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- A FACILE CONVERSION OF SULFOXIMINES AND SULFONEDIIMINES TO SULFOXIDES AND SULFILIMINES WITH TERT-BUTYL NITRITE
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N-Unsubstituted sulfoximines and N-mono-tosylsulfonediimines were found to react readily with tert-butyl nitrite to give the corresponding sulfoxides and N-tosylsulfilimines in high yields with no racemization.
- Akutagawa, Kunihiko,Furukawa, Naomichi,Oae, Shigeru
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p. 369 - 374
(2007/10/02)
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