Synthesis and structure of novel sulfur bridged cyclic di- and tetraalkynes

S. Braverman; M. Cherkinsky; M. L. Birsa; S. Tichman; I. Goldberg

doi:10.1016/s0040-4039(01)01554-4

Synthesis and structure of novel sulfur bridged cyclic di- and tetraalkynes

S. Braverman, M. Cherkinsky, M. L. Birsa, S. Tichman, I. Goldberg

Department of Chemistry

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

18 Scopus citations

Abstract

Some novel sulfur bridged 13- to 30-membered cyclic di- and tetraalkynes derived from 1,2-, 1,3- and 1,4-dihydroxybenzene and 1,2-bis(bromomethyl)benzene were synthesized and their structures confirmed by X-ray analysis. The unexpected formation of 2,6-divinyl-1,4-dithiin during Na₂S/alumina induced cyclization was also observed and the reaction mechanism is discussed.

Original language	English
Pages (from-to)	7485-7488
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	42
DOIs	https://doi.org/10.1016/s0040-4039(01)01554-4
State	Published - 15 Oct 2001

Bibliographical note

Funding Information:
The financial support of this study by the Israel Science Foundations is gratefully acknowledged. One of us (M.L.B.) is also grateful for the award of a Vatat postdoctoral fellowship.

Funding

The financial support of this study by the Israel Science Foundations is gratefully acknowledged. One of us (M.L.B.) is also grateful for the award of a Vatat postdoctoral fellowship.

Funders	Funder number
Israel Science Foundation

Keywords

1,4-dithiin
Cyclic dipropargylic sulfide
Cyclic tetrapropargylic sulfide

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10.1016/s0040-4039(01)01554-4

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abstract = "Some novel sulfur bridged 13- to 30-membered cyclic di- and tetraalkynes derived from 1,2-, 1,3- and 1,4-dihydroxybenzene and 1,2-bis(bromomethyl)benzene were synthesized and their structures confirmed by X-ray analysis. The unexpected formation of 2,6-divinyl-1,4-dithiin during Na2S/alumina induced cyclization was also observed and the reaction mechanism is discussed.",

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AU - Cherkinsky, M.

AU - Birsa, M. L.

AU - Tichman, S.

AU - Goldberg, I.

N1 - Funding Information: The financial support of this study by the Israel Science Foundations is gratefully acknowledged. One of us (M.L.B.) is also grateful for the award of a Vatat postdoctoral fellowship.

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N2 - Some novel sulfur bridged 13- to 30-membered cyclic di- and tetraalkynes derived from 1,2-, 1,3- and 1,4-dihydroxybenzene and 1,2-bis(bromomethyl)benzene were synthesized and their structures confirmed by X-ray analysis. The unexpected formation of 2,6-divinyl-1,4-dithiin during Na2S/alumina induced cyclization was also observed and the reaction mechanism is discussed.

AB - Some novel sulfur bridged 13- to 30-membered cyclic di- and tetraalkynes derived from 1,2-, 1,3- and 1,4-dihydroxybenzene and 1,2-bis(bromomethyl)benzene were synthesized and their structures confirmed by X-ray analysis. The unexpected formation of 2,6-divinyl-1,4-dithiin during Na2S/alumina induced cyclization was also observed and the reaction mechanism is discussed.

KW - 1,4-dithiin

KW - Cyclic dipropargylic sulfide

KW - Cyclic tetrapropargylic sulfide

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Synthesis and structure of novel sulfur bridged cyclic di- and tetraalkynes

Abstract

Bibliographical note

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Keywords

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