Sulfur Ylides (Sulfuranes) from Active Methylene Compounds and Dimethyl Sulfoxide; A Useful Alternative to Known Methods

Schank, Kurt; Schuhknecht, C.

doi:10.1055/s-1978-24850

Cited by 17 publications

(2 citation statements)

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“…In 1978, Schank and Schuhknecht used 1,2-oxathiolan-5-one 2,2-dioxide (sulfopropanoic anhydride) (4) instead of DCC as the activator to activate DMSO (2a). [31] Four cyclic sulfonium diacylmethylides 3a and 6 were prepared in satisfactory yields. In contrast to DCU, the generated byproduct 3-sulfopropanoic acid has excellent solubility in water and can be removed by simple washing.…”

Section: Active Methylene Compounds As Substratesmentioning

confidence: 97%

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Synthesis of Sulfo(xo)nium Diacylmethylides

Fu,

2024

Eur J Org Chem

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Sulfo(xo)nium diacylmethylides (sulfur ylides) are simple, stable, readily prepared, and versatile synthons. Compared with the sulfo(xo)nium monoacylmethylides, they can be compatible with more rigorous reaction conditions and showcase unique characteristics due to their excellent stability. This concept article provides an account for the syntheses of sulfo(xo)nium diacylmethylides, including the utilization of active methylene compounds, carbene precursors, sulfo(xo)nium monoacylmethylides, and electron‐deficient alkynes as substrates, with discussions on substrate scopes, proposed mechanisms, selected product examples, and applications. Challenges for further exploration and prospect on sulfo(xo)nium diacylmethylides in the future are also suggested.

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Section: Active Methylene Compounds As Substratesmentioning

confidence: 97%

“…In 1978, Schank and Schuhknecht used 1,2‐oxathiolan‐5‐one 2,2‐dioxide (sulfopropanoic anhydride) ( 4 ) instead of DCC as the activator to activate DMSO ( 2a ) [31] . Four cyclic sulfonium diacylmethylides 3a and 6 were prepared in satisfactory yields.…”

Section: Synthesis Of Sulfo(xo)nium Diacylmethylidesmentioning

confidence: 99%