Tandem rearrangement, cyclization and aromatization of sulfur bridged propargylic systems

Samuel Braverman; Yossi Zafrani; Hugo E. Gottlieb

doi:10.1016/s0040-4039(00)00221-5

Tandem rearrangement, cyclization and aromatization of sulfur bridged propargylic systems

Samuel Braverman, Yossi Zafrani, Hugo E. Gottlieb

Department of Chemistry

Bar-Ilan University

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

28 Scopus citations

Abstract

The reactivity of some novel Π-conjugated bis-propargylic sulfides, sulfoxides and sulfones under basic conditions has been investigated. These compounds undergo isomerization to the corresponding diallenes, followed by a tandem cyclization and aromatization of the latter via a diradical intermediate. Surprisingly, we have found that the rate of the cyclization step was independent of the nature of the bridging functionality. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	2675-2678
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	15
DOIs	https://doi.org/10.1016/s0040-4039(00)00221-5
State	Published - 8 Apr 2000

Bibliographical note

Funding Information:
The financial support of this study by the Israel Science Foundation is gratefully acknowledged.

Funding

The financial support of this study by the Israel Science Foundation is gratefully acknowledged.

Funders	Funder number
Israel Science Foundation

Keywords

Cyclization
Diallenes
Diradicals
Diynes
Sulfur compounds

Access to Document

10.1016/s0040-4039(00)00221-5

Cite this

@article{80e802ef355a4762bfbcf36db5f46afa,

title = "Tandem rearrangement, cyclization and aromatization of sulfur bridged propargylic systems",

abstract = "The reactivity of some novel Π-conjugated bis-propargylic sulfides, sulfoxides and sulfones under basic conditions has been investigated. These compounds undergo isomerization to the corresponding diallenes, followed by a tandem cyclization and aromatization of the latter via a diradical intermediate. Surprisingly, we have found that the rate of the cyclization step was independent of the nature of the bridging functionality. (C) 2000 Elsevier Science Ltd.",

keywords = "Cyclization, Diallenes, Diradicals, Diynes, Sulfur compounds",

author = "Samuel Braverman and Yossi Zafrani and Gottlieb, {Hugo E.}",

note = "Funding Information: The financial support of this study by the Israel Science Foundation is gratefully acknowledged.",

year = "2000",

month = apr,

day = "8",

doi = "10.1016/s0040-4039(00)00221-5",

language = "אנגלית",

volume = "41",

pages = "2675--2678",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "15",

}

TY - JOUR

T1 - Tandem rearrangement, cyclization and aromatization of sulfur bridged propargylic systems

AU - Braverman, Samuel

AU - Zafrani, Yossi

AU - Gottlieb, Hugo E.

N1 - Funding Information: The financial support of this study by the Israel Science Foundation is gratefully acknowledged.

PY - 2000/4/8

Y1 - 2000/4/8

N2 - The reactivity of some novel Π-conjugated bis-propargylic sulfides, sulfoxides and sulfones under basic conditions has been investigated. These compounds undergo isomerization to the corresponding diallenes, followed by a tandem cyclization and aromatization of the latter via a diradical intermediate. Surprisingly, we have found that the rate of the cyclization step was independent of the nature of the bridging functionality. (C) 2000 Elsevier Science Ltd.

AB - The reactivity of some novel Π-conjugated bis-propargylic sulfides, sulfoxides and sulfones under basic conditions has been investigated. These compounds undergo isomerization to the corresponding diallenes, followed by a tandem cyclization and aromatization of the latter via a diradical intermediate. Surprisingly, we have found that the rate of the cyclization step was independent of the nature of the bridging functionality. (C) 2000 Elsevier Science Ltd.

KW - Cyclization

KW - Diallenes

KW - Diradicals

KW - Diynes

KW - Sulfur compounds

UR - http://www.scopus.com/inward/record.url?scp=0034620924&partnerID=8YFLogxK

U2 - 10.1016/s0040-4039(00)00221-5

DO - 10.1016/s0040-4039(00)00221-5

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:0034620924

SN - 0040-4039

VL - 41

SP - 2675

EP - 2678

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

Tandem rearrangement, cyclization and aromatization of sulfur bridged propargylic systems

Abstract

Bibliographical note

Funding

Keywords

Access to Document

Other files and links

Fingerprint

Cite this