.alpha.-Substituted sulfoxides. IV. Phenyl diazomethyl sulfoxide (phenylsulfinyldiazomethane) and phenylsulfinyl carbene, a highly stereoselective cyclopropanating agent

Venier, Clifford G.; Barager, Howard J.; Ward, Mark A.

doi:10.1021/ja00844a064

Cited by 28 publications

(4 citation statements)

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“…The precursor bis(chloromethyl) sulfoxide was prepared based on the procedure described by Venier et al. using thionyl chloride and diazomethane 20. [D 4 ]‐1,3‐Dithietan‐1,3‐dioxide was obtained by carrying out the following procedure twice: dissolving the parent compound in a large excess of slightly alkaline D 2 O, keeping the solution for 2 h at 70 °C, and evaporating the solvent under reduced pressure at 0 °C.…”

Section: Methodsmentioning

confidence: 99%

A Formal Carbon–Sulfur Triple Bond: HCSOH

et al. 2009

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Section: Methodsmentioning

confidence: 99%

A Formal Carbon–Sulfur Triple Bond: HCSOH

et al. 2009

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“…Both diazo transfer to sulfoxides [623] and treatment of sulfinyl chlorides with diazomethane [624] failed to give simple isolable α-diazosulfoxides, or products that were indicative of a hetero Wolff rearrangement. The first reported stable diazosulfoxides were the cephalosporin derivatives 884.…”

Section: α-Diazophosphane Oxides -Phosphinates and Related Substratesmentioning

confidence: 99%

100 Years of the Wolff Rearrangement

2002

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The conversion of α‐diazo ketones into ketenes, and products derived therefrom, was discovered by Wolff in 1902. Major applications of the Wolff rearrangement, such as the Arndt−Eistert reaction (homologation of carboxylic acids) and the ring contraction of cyclic ketones, have been with us for some while. Nevertheless, substantial progress has been made recently. The reaction mechanism has been explored by means of matrix isolation, time‐resolved spectroscopy, and computation. Full retention of configuration of the migrating group has been established by using enantioselective chromatography. The Arndt−Eistert reaction has witnessed a renaissance in the field of natural products, in particular β‐amino acids and β‐peptides. Ring‐contracting Wolff rearrangements and ketene cycloadditions have been applied in syntheses of increasingly complex, biologically active target molecules. These accomplishments, as well as unsolved problems, are addressed in the present review. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

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“…Introduction. Sulfinyl carbenes are a new and largely unstudied class of organic reactive intermediates (Venier, Barager & Ward, 1975). In a study of their reactions with alkynes, adducts with a stoichiometry of two molecules of sulfinyl carbene to one molecule of acetylene were isolated (Venier & Beckhaus, 1978).…”

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confidence: 99%