SYNTHETIC STUDIES ON THE 1,6-METHANO[10]ANNULENE SKELETON - A NEW ROUTE THAT PROVIDES DERIVATIVES SUBSTITUTED AT THE BRIDGE AND ON THE ANNULENE RING

被引：13

作者：

BARRETT, DG ^{[1
]}

LIANG, GB ^{[1
]}

MCQUADE, DT ^{[1
]}

DESPER, JM ^{[1
]}

SCHLADETZKY, KD ^{[1
]}

GELLMAN, SH ^{[1
]}

机构：

[1] UNIV WISCONSIN,DEPT CHEM,MADISON,WI 53706

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1994年 / 116卷 / 23期

关键词：

D O I：

10.1021/ja00102a020

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new synthetic route to the 1,6-methano[10]annulene skeleton has been developed. The key step in this route is the semi-benzylic Favorskii rearrangement of a [4.4.2]propellane to a [4.4.1]propellane. The methodology discussed here provides access to 1,6-methano[10]annulene derivatives bearing substituents on both the bridge carbon and the annulene ring. Control of the relative positioning of these appendages is achieved by introducing the annulene substituent via cuprate addition to an allylic lactone.

引用

页码：10525 / 10532

页数：8

共 23 条

[1]

BARRET DG, 1993, THESIS U WISCONSIN M

[2] A NEW SYNTHESIS OF METHANOBRIDGED ANNULENES - ACCESS TO HIGHLY SUBSTITUTED DERIVATIVES [J].