Reaction of ene-bis(phosphinylallenes): [2+2] versus [4+2] cycloaddition

被引：28

作者：

Kitagaki, Shinji ^{[1
]}

Okumura, Yuki ^{[1
]}

Mukai, Chisato ^{[1
]}

机构：

[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Div Pharmaceut Sci, Kanazawa, Ishikawa 9201192, Japan

来源：

TETRAHEDRON | 2006年 / 62卷 / 44期

关键词：

bisallenes; 2+2] cycloaddition; naphtho[b]cyclobutenes; 4+2] cycloaddition;

D O I：

10.1016/j.tet.2006.08.083

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of ene-bis(phosphinylallenes), derived from ene-bis(propargyl alcohols) and chlorodiphenylphosphine, was investigated. Benzene-bridged bis(phosphinylallenes) exclusively gave intramolecular [2+2] cycloadducts in the presence of dimethyl fumarate in sharp contrast to the reaction of benzene-bridged bis(sulfinylallenes), which gave the corresponding [4+2] cycloadducts. On the other hand, substituted ethylene- or five-membered heterocycle-bridged bis(phosphinylallenes) provided [4+2] cycloadducts. Reaction of benzene-bridged diallene bearing both a sulfinyl group and a phosphinyl group on the two allenyl groups was also described. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：10311 / 10320

页数：10

共 24 条

[1]

BENEFRAIM DA, 1963, TETRAHEDRON LETT, P313

[2]

BOWES CM, 1973, TETRAHEDRON LETT, P3181

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