On the control of sulphenylations at carbon

Grossert, J. Stuart; Dubey, P. K.

doi:10.1039/c39820001183

Cited by 36 publications

(40 citation statements)

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“…This reaction is a convenient method of synthesizing various aketo sulfides from a single organosulfur compound without using base or reactive sulfenylating reagents. [5][6][7][8][9][10][11][12][13] It is likely that the oxidative addition of thioketones to the rhodium complex provides the C-Rh-SR intermediates, which undergo alkylthio exchange forming other C-Rh-SRЈ complexes. aAlkylthio exchange ketones are liberated by the reductive elimination with regeneration of rhodium catalyst.…”

Section: Regular Articlementioning

confidence: 99%

Rhodium-Catalyzed Organothio Exchange Reaction of .ALPHA.-Organothioketones with Disulfides

Arisawa

Toriyama

Yamaguchi

2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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RhH(PPh(3))(4) and 1,2-bis(diphenylphosphino)ethane (dppe) catalyzed the organothio exchange reaction of α-organothioketones and organic disulfides. The reaction was affected by the structure of the substrate: α-phenylthio and α-alkylthio aryl ketones reacted effectively with diaryl and dialkyl disulfides; α-phenylthio dialkyl ketones reacted with diaryl disulfides but not with dialkyl disulfides; diaryl disulfides with electron-donating p-substituents were more reactive than those with electron-withdrawing p-substituents.

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Section: Regular Articlementioning

confidence: 99%

Rhodium-Catalyzed Organothio Exchange Reaction of .ALPHA.-Organothioketones with Disulfides

Arisawa

Toriyama

Yamaguchi

2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Those from entries 4-7, 15,21, 23,24, and 28 were available from previous work (1 1, 12, 25). All other compounds were prepared by literature procedures and their purities were checked using both nmr spectroscopy and comparison of melting points with the reported values (26)(27)(28)(29).…”

Section: Preparation Of the Sulphonesmentioning

confidence: 99%

Sulphur-33 nuclear magnetic resonance spectroscopy of sulphones

Hoyle¹,

Grossert²,

Hooper³

et al. 1986

Can. J. Chem.

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The sulphur-33 nmr spectra of 28 sulphones were measured in deuterochloroform solutions at 27.716172 MHz. The spectra were referenced with respect to an external aqueous ammonium sulphate solution and the chemical shifts lay in the range 0 ± 20 ppm, with many lines having a half-height width of less than 200 Hz. Instrumental parameters that affect the spectra were studied. Some of the sulphur-33 resonances can be correlated well with carbon-13 or oxygen-17 resonances in appropriate analogous compounds, and with the Taft σ* parameter.

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“…The range of polyfunctional sulfones obtained in this study forms a useful series in which to study spectroscopic properties and we have, in addition, determined crystal structures of certain selected compounds by X-ray diffraction techniques. In subsequent papers we will describe reactions of a-halo-P-ketosulfones with nucleophiles having varying degrees of hardness on the HSAB scale,' and report on direct sulfenylation reactions to give a-sulfenylated-P-ketosulfones (9).…”

Section: Introductionmentioning

confidence: 99%

The preparation, spectral properties, structures, and base-induced cleavage reactions of some α-halo-β-ketosulfones

Grossert¹,

Dubey²,

Gill³

et al. 1984

Can. J. Chem.

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The halogenation of β-ketosulfones such as α-methylsulfonylacetophenone (1) and benzenesulfonylacetone (10) can be effected with sulfuryl chloride or pyridinium bromide perbromide. Regiochemical control can be achieved by control of stoichiometry and/or the reaction conditions. Detailed 1H and 13C nmr, and mass spectra are recorded for a series of halogenated β-ketosulfones, together with structures by X-ray crystallography for 1, 2-chloro-2-methylsulfonyl-1-phenylethanone (2), chloromethyl methyl sulfone (4), and α-chloroacetophenone (21). Results from these studies are used to suggest a reason for the difficulty associated with substitution reactions of α-halosulfones.

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On the control of sulphenylations at carbon

Abstract: Controlled monosulphenylation a t carbon adjacent to electron-withdrawing groups can be achieved by the controlled reduction of readily available bis-sulphenylated products.

Cited by 36 publications

References 0 publications

Rhodium-Catalyzed Organothio Exchange Reaction of .ALPHA.-Organothioketones with Disulfides

Rhodium-Catalyzed Organothio Exchange Reaction of .ALPHA.-Organothioketones with Disulfides

Sulphur-33 nuclear magnetic resonance spectroscopy of sulphones

The preparation, spectral properties, structures, and base-induced cleavage reactions of some α-halo-β-ketosulfones

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