Synthesis of 1,2-dithiolane-3,5-diones and thietane-2,4-diones

Schauble, J. Herman; Williams, J. L. R.

doi:10.1021/jo00980a036

Cited by 11 publications

(3 citation statements)

References 2 publications

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“…Pure disulfide XII was isolated by column chromatography on silica gel. Unfortunately, we failed to effect desulfurization of disulfide XII by its reaction with triphenylphosphine by the procedure in [12]:…”

Section: äääääääääääämentioning

confidence: 99%

4,4-Dimethyl-1,4-thiasilinane and Its S-Functional Derivatives

2005

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Synthetic approaches to 4,4-dimethyl-1,4-thiasilinane and its S-functional derivatives, 4,4-dimethyl-1,4-thiasilinane S-oxide, 4,4-dimethyl-1,4-thiasilinane S,S-dioxide, 4,4-dimethyl-1-(phenylsulfonylimino)-1,4-thiasilinane, and 1,4,4-trimethyl-1,4-thiasilinan-1-ylium iodide, were studied. The S-functional derivatives of 4,4-dimethyl-4-thiasilinane, unlike 3,3-dimethyl-3-thiasilinane, are hydrolytically stable.Thiasilinanes form an interesting class of heteroatomic cyclohexane derivatives. Thiasilinanes differ from earlier studied diheterocyclohexanes (dioxanes, dithianes, and oxathianes) in that they contain two heteroatoms of different nature: sulfur with a lone electron pair and silicon that exerts a strong inductive effect and, at the same time, has vacant d orbitals.Thiasilinanes have poorly been studied [136], while their S-functional derivatives have been unknown. In the course of the research into the properties and transformations of silathiacycloalkanes we have synthesized 3,3-dimethyl-1,3-thiasilinane S-oxide [7], 2,3,3-trimethyl-1,3-thiasilinane S-oxide, 2,3,3-tri-ÄÄÄÄÄÄÄÄÄÄÄÄ methyl-1,3-thiasilinane S,S-dioxide [8], 3,3-dimethyl-1-(phenylsulfonylimino)-1,3-thiasilinane, and 1,3,3-trimethyl-1,3-thiasilinan-1-ylium iodide [9, 10], and studied their transformations [10]. These works have primarily focused on 1,3-thiasilinanes; the only available information on 1,4-thiasilinanes related to the synthesis of 1,4-thiasilinane and its sulfonium salt, 1,4,4-trimethyl-1,4-thiasilinan-1-ylium iodide [4]. Proceeding with this research, in the present work we developed new synthetic approaches to 4,4-dimethyl-4-thiasilinane (I), synthesized their S-oxides II3V, and studied their hydrolytic stability.

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Section: äääääääääääämentioning

confidence: 99%

4,4-Dimethyl-1,4-thiasilinane and Its S-Functional Derivatives

2005

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“…cases 3a was identified by nmr and by glpc using the retention time and the technique of peak potentiation with an authentic sample. 16 The l,3-dithiane-4,6-diones could not be detected by nmr.…”

Section: Methodsmentioning

confidence: 93%

“…The thietanediones 3a and 3b were identified by comparison of their ir and nmr spectra and glpc retention times with those for authentic samples. 16 Stability of la to Sulfuric Acid or Boron Trifluoride Etherate. To 0.5 ml of a saturated solution of concentrated H2SO4 in benzene-de in an nmr tube was added 50 mg of pure la.…”

Section: Methodsmentioning

confidence: 99%