A novel synthesis of thiophenes from allenic sulfones involving α,β-unsaturated sulfines as intermediates

S. Braverman; P. F.T.M. van Asten; J. B. van der Linden; B. Zwanenburg

doi:10.1016/S0040-4039(00)79399-3

A novel synthesis of thiophenes from allenic sulfones involving α,β-unsaturated sulfines as intermediates

S. Braverman, P. F.T.M. van Asten, J. B. van der Linden, B. Zwanenburg

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

A new method for the synthesis of α,β-unsaturated sulfines by a Peterson alkylidenation of sulfur dioxide is described. The required α-silyl carbanions are generated by heteroconjugate addition of alkyllithium to α-trimethylsitylated aIlenic sulfones. The conjugated vinylsulfines thus prepared undergo a rapid and unprecedented cycloaromatization to thiophene derivatives. A mechanism for this remarkable conversion is presented.

Original language	English
Pages (from-to)	3867-3870
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	31
DOIs	https://doi.org/10.1016/S0040-4039(00)79399-3
State	Published - 29 Jul 1991
Externally published	Yes

Bibliographical note

Funding Information:
Acknowledgement: This investigation was supported by the Netherlands Foundation of Chemical Research with financial aid from the NetherlandsO rganization for Scientific Research (NWO). One of us (S.B.) expresses his appreciationf or the award of an NWO-visiting professorship.

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10.1016/S0040-4039(00)79399-3

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abstract = "A new method for the synthesis of α,β-unsaturated sulfines by a Peterson alkylidenation of sulfur dioxide is described. The required α-silyl carbanions are generated by heteroconjugate addition of alkyllithium to α-trimethylsitylated aIlenic sulfones. The conjugated vinylsulfines thus prepared undergo a rapid and unprecedented cycloaromatization to thiophene derivatives. A mechanism for this remarkable conversion is presented.",

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note = "Funding Information: Acknowledgement: This investigation was supported by the Netherlands Foundation of Chemical Research with financial aid from the NetherlandsO rganization for Scientific Research (NWO). One of us (S.B.) expresses his appreciationf or the award of an NWO-visiting professorship.",

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AU - van Asten, P. F.T.M.

AU - van der Linden, J. B.

AU - Zwanenburg, B.

N1 - Funding Information: Acknowledgement: This investigation was supported by the Netherlands Foundation of Chemical Research with financial aid from the NetherlandsO rganization for Scientific Research (NWO). One of us (S.B.) expresses his appreciationf or the award of an NWO-visiting professorship.

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AB - A new method for the synthesis of α,β-unsaturated sulfines by a Peterson alkylidenation of sulfur dioxide is described. The required α-silyl carbanions are generated by heteroconjugate addition of alkyllithium to α-trimethylsitylated aIlenic sulfones. The conjugated vinylsulfines thus prepared undergo a rapid and unprecedented cycloaromatization to thiophene derivatives. A mechanism for this remarkable conversion is presented.

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A novel synthesis of thiophenes from allenic sulfones involving α,β-unsaturated sulfines as intermediates

Abstract

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