Synthesis and Isolation of α-Oxo Sulfines

Damen, Theodorus J. G.; Zwanenburg, B.

doi:10.1080/10426509708545528

Phosphorus, Sulfur, and Silicon and the Related Elements

1997

DOI: 10.1080/10426509708545528

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Synthesis and Isolation of α-Oxo Sulfines

Theodorus J. G. Damen

B. Zwanenburg

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1999

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Advances in Sulfine Chemistry

Zwanenburg¹,

Damen²,

Philipse³

et al. 1999

Phosphorus, Sulfur, and Silicon and the Related Elements

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Sulfines (thione S-oxides) are nonlinear sulfur centered heterocumulenes formally derived from sulfur dioxide by replacing one oxygen by a carbon atom. In the introduction historical highlights are presented. A section is devoted to some recent developments regarding the synthesis of sulfines, viz. via oxidation by dimethyl dioxirane, and the reaction of silyl enol ethers and active methylene compounds, respectively, with thionyl chloride in the presence of a tertiairy amine base. Enethiolization of sulfines to vinylsulfenic acid is discussed in terms of its entrapment by an intramolecular reaction with an olefin. In this context also the optical integrity of sulfines having a stereogenic center at C-cc is described. In the final section the Diels-Alder type cycloaddition reaction to give dihydrothiopyran S-oxides, with special focus on the asymmetric induction, is reported.

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Advances in Sulfine Chemistry

Zwanenburg¹,

Damen²,

Philipse³

et al. 1999

Phosphorus, Sulfur, and Silicon and the Related Elements

View full text Add to dashboard Cite

show abstract

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Synthesis and Isolation of α-Oxo Sulfines

Cited by 1 publication

References 2 publications

Advances in Sulfine Chemistry

Advances in Sulfine Chemistry

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