Michael additions to 3(2H)-thiophenone 1,1-dioxide

Hofsløkken, Nini U.; Flock, Solveig; Skattebøl, Lars

doi:10.1016/0040-4039(95)02088-8

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β-Acylvinyl Cationic Synthons1

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1996

2022

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Cited by 7 publications

(2 citation statements)

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“…Accordingly, β-( p -toluenesulfonyl)-α,β-unsaturated esters and amides 448 react regio- and stereoselectively with organomagnesium compounds and sodium malonate 238a or even sodium alcoholates or thiolates 238b to yield β-substituted α,β-enoates or enamides 449 or 450 , respectively (Scheme ). This methodology has been applied to the synthesis of natural antifungal sinharine 452 , starting from sulfonyl acrylamide 451 (Scheme ) 238b…”

Section: β-Acylvinyl Cationic Synthonsmentioning

confidence: 99%

Acylvinyl and Vinylogous Synthons

Chinchílla

Nájera

2000

Chem. Rev.

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Section: β-Acylvinyl Cationic Synthonsmentioning

confidence: 99%

Acylvinyl and Vinylogous Synthons

Chinchílla

Nájera

2000

Chem. Rev.

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“…84Michael Additions to 3(2H)-Thiophenone 1,1-Dioxide.The addition of thiols and amines to 3(2H)-thiophenone 1,1-dioxide takes place with extrusion of sulfur dioxide, furnishing in high yields the corresponding vinyl sulfides and enamines. Addition of 1,3-propanedithiol affords the corresponding acetal (eq 29) 85. …”

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1,3-Propanedithiol

Conrow

Huérou

2006

Encyclopedia of Reagents for Organic Synthesis

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Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

Guziec

2022

Organic Reactions

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Extrusion reactions may be defined as chemical reactions in which an atom or small molecular fragment Y connected to two other atoms W and Z is lost from a molecule, leading to a product in which W becomes directly bonded to Z. Cheletropic reactions that afford aromatic or conjugated π systems by loss of a stable atomic or molecular fragment have also been classified as extrusion reactions. Typically, the fragments liberated in these reactions are small, stable inorganic molecules or atoms such as carbon monoxide, carbon dioxide, sulfur, sulfur monoxide, sulfur dioxide, selenium, tellurium, oxygen and nitrogen. This chapter primarily deals with the synthesis of arenes, heterocycles, 1,3‐dienes and polyenes using such extrusion processes. The utility of these reactions in the synthesis of sterically hindered molecules, dendrimers, pheromones, and other natural products are highlighted. The use of extrusion reactions for the “Click and Release” approach in drug development is also introduced.

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Michael additions to 3(2H)-thiophenone 1,1-dioxide

Cited by 7 publications

References 13 publications

Acylvinyl and Vinylogous Synthons

Acylvinyl and Vinylogous Synthons

1,3-Propanedithiol

Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

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