ACID-CATALYZED REARRANGEMENT OF PHENYLSUBSTITUTED 1,3-BISHOMOCUBANONE VIA SEVERAL EQUILIBRATING NONCLASSICAL BICYCLOBUTONIUM IONS

被引：1

作者：

OGINO, T ^{[1
]}

OHTAKI, N ^{[1
]}

YAMAI, S ^{[1
]}

WADA, F ^{[1
]}

AWANO, K ^{[1
]}

机构：

[1] NAGAOKA COLL TECHNOL,DEPT IND CHEM,NAGAOKA,NIIGATA 940,JAPAN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(00)76970-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Phenylpentacyclo[5.3.0.0(2,5).0(3,9).0(4,8)]decan-6-one in acetic acid undergoes H2SO4-catalyzed rearrangement to give two isomeric acetoxyketones having a novel tricyclo[5.2.1.0(4,8)]dec-2-ene ring system besides a small amount of 2,3-dihydro-7-phenyl-1(8H)-azulenone. The formation of the acetoxyketones can best be accounted by assuming equilibration of several structurally different non-classical bicyclobutonium ion intermediates.

引用

页码：4793 / 4796

页数：4

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