A CYCLOBUTANONE-BASED TANDEM FREE-RADICAL REARRANGEMENT

被引：5

作者：

DOWD, P

ZHANG, W

MAHMOOD, K

机构：

[1] Department of Chemistry University of Pittsburgh, Pittsburgh

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 31期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)77247-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Free radical reaction of endo-haroalkylbicyclo[4.2.0]oct-2-en-7-ones 1 and 11 leads to sequential rearrangement and formation of the novel, bridged tricyclic ketones 2 and 13. A mechanism for this unusual transformation is proposed.

引用

页码：5563 / 5566

页数：4

共 30 条

[1] REARRANGEMENT OF SUITABLY CONSTITUTED ARYL, ALKYL, OR VINYL RADICALS BY ACYL OR CYANO GROUP MIGRATION [J].

BECKWITH, ALJ ;

OSHEA, DM ;

WESTWOOD, SW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2565-2575

[2] CYANO OR ACYL GROUP MIGRATION BY CONSECUTIVE HOMOLYTIC ADDITION AND BETA-FISSION [J].

BECKWITH, ALJ ;

OSHEA, DM ;

GERBA, S ;

WESTWOOD, SW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (09) :666-667

[3] KINETICS AND MECHANISM OF THE EXO CYCLIZATIONS OF OMEGA-FORMYLALKYL RADICALS [J].

BECKWITH, ALJ ;

HAY, BP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) :2674-2681

[4] COPPER-CATALYZED ADDITIONS OF ORGANIC POLYHALIDES TO OLEFINS - A VERSATILE SYNTHETIC TOOL [J].

BELLUS, D .

PURE AND APPLIED CHEMISTRY, 1985, 57 (12) :1827-1838

[5] TANDEM FREE-RADICAL RING EXPANSION AND 5-EXO-DIG 5-HEXYNYL RADICAL CYCLIZATION - A USEFUL APPROACH TO FUSED BICYCLIC CARBOCYCLES [J].

BOGER, DL ;

MATHVINK, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (20) :5442-5444

[6]

BOWMAN WR, 1992, TETRAHEDRON, V48, P4027

[7] THE CHEMISTRY OF TAXANES - SKELETAL REARRANGEMENTS OF BACCATIN DERIVATIVES VIA RADICAL INTERMEDIATES [J].

CHEN, SH ;

HUANG, S ;

GAO, Q ;

GOLIK, J ;

FARINA, V .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) :1475-1484

[8] RADICAL CLEAVAGE OF CYCLOBUTANES - ALTERNATIVE ROUTES TO (+/-)-SILPHINENE [J].

CRIMMINS, MT ;

MASCARELLA, SW .

TETRAHEDRON LETTERS, 1987, 28 (43) :5063-5066

[9] A FRAGMENTATION-REARRANGEMENT SEQUENCE OF CYCLOBUTYLCARBINYL RADICALS [J].

CRIMMINS, MT ;

DUDEK, CM ;

CHEUNG, AWH .

TETRAHEDRON LETTERS, 1992, 33 (02) :181-184

[10] NEW REAGENTS FOR RADICAL ALLYLATIONS [J].

CURRAN, DP ;

YOO, BW .

TETRAHEDRON LETTERS, 1992, 33 (46) :6931-6934

← 1 2 3 →