Tandem rearrangement, cyclization and aromatization of sulfur bridged propargylic systems

被引：26

作者：

Braverman, S ^{[1
]}

Zafrani, Y ^{[1
]}

Gottlieb, HE ^{[1
]}

机构：

[1] Bar Ilan Univ, Dept Chem, IL-52900 Ramat Gan, Israel

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 15期

基金：

以色列科学基金会;

关键词：

cyclization; diradicals; diynes; diallenes; sulfur compounds;

D O I：

10.1016/S0040-4039(00)00221-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactivity of some novel pi-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. All rights reserved.

引用

页码：2675 / 2678

页数：4

共 21 条

[1]

[Anonymous], 1984, COMPREHENSIVE HETERO

[2]

BRAVERMAN S, 1967, ISR J CHEM, V5, P125

[3]

BRAVERMAN S, 1978, TETRAHEDRON LETT, P1493

[4]

BRAVERMAN S, 1976, TETRAHEDRON LETT, P3181

[5] THERMAL REARRANGEMENTS OF ALLENES - SYNTHESIS AND MECHANISM OF CYCLOAROMATIZATION OF PI-BRIDGED AND HETEROATOM BRIDGED DIALLENES [J].

BRAVERMAN, S ;

DUAR, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (15) :5830-5837

[6] NOVEL CYCLIZATION OF DIALLENIC SULFONES [J].

BRAVERMAN, S ;

SEGEV, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (04) :1245-1247

[7]

BRAVERMAN S, 1988, CHEM SULFONES SULFOX, pCH14

[8]

BRAVERMAN S, 1988, CHEM SULFONES SULFOX, pCH13

[9]

BRAVERMAN S, UNPUB

[10]

CHENG YSP, 1985, ISR J CHEM, V26, P101

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