Tandem cyclization and aromatization of sulfur bridged diallenic systems: Potential enediyne models

Samuel Braverman; Yossi Zafrani; Tatiana Pechenik

doi:10.1080/10426509908546472

Tandem cyclization and aromatization of sulfur bridged diallenic systems: Potential enediyne models

Samuel Braverman
, Yossi Zafrani
, Tatiana Pechenik

Department of Chemistry

Bar-Ilan University

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

Abstract

The synthesis and base catalyzed rearrangement of bis-γ-phenylpropargyl sulfone, sulfoxide and sulfonium salts are described. In contrast to the first two compounds which undergo a fast acetylene to allene isomerization followed by a tandem cyclization and aromatization via a diradical mechanism, the latter compound undergoes a [2,3]-sigmatropic shift via the corresponding ylide intermediate.

Original language	English
Pages (from-to)	363-364
Number of pages	2
Journal	Phosphorus, Sulfur and Silicon and the Related Elements
Volume	153-154
DOIs	https://doi.org/10.1080/10426509908546472
State	Published - 1999

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title = "Tandem cyclization and aromatization of sulfur bridged diallenic systems: Potential enediyne models",

abstract = "The synthesis and base catalyzed rearrangement of bis-γ-phenylpropargyl sulfone, sulfoxide and sulfonium salts are described. In contrast to the first two compounds which undergo a fast acetylene to allene isomerization followed by a tandem cyclization and aromatization via a diradical mechanism, the latter compound undergoes a [2,3]-sigmatropic shift via the corresponding ylide intermediate.",

author = "Samuel Braverman and Yossi Zafrani and Tatiana Pechenik",

year = "1999",

doi = "10.1080/10426509908546472",

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AU - Zafrani, Yossi

AU - Pechenik, Tatiana

PY - 1999

Y1 - 1999

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AB - The synthesis and base catalyzed rearrangement of bis-γ-phenylpropargyl sulfone, sulfoxide and sulfonium salts are described. In contrast to the first two compounds which undergo a fast acetylene to allene isomerization followed by a tandem cyclization and aromatization via a diradical mechanism, the latter compound undergoes a [2,3]-sigmatropic shift via the corresponding ylide intermediate.

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DO - 10.1080/10426509908546472

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AN - SCOPUS:0033234339

SN - 1042-6507

VL - 153-154

SP - 363

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JO - Phosphorus, Sulfur and Silicon and the Related Elements

JF - Phosphorus, Sulfur and Silicon and the Related Elements

ER -

Tandem cyclization and aromatization of sulfur bridged diallenic systems: Potential enediyne models

Abstract

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