INTRAMOLECULAR ADDITION OF CARBON-CENTERED TINTHIOIMIDOYL RADICALS TO CARBON CARBON DOUBLE-BONDS - SYNTHESIS OF GAMMA-THIOLACTAMS AND DELTA-THIOLACTAMS

被引：55

作者：

BACHI, MD

DENENMARK, D

机构：

[1] Department of Organic Chemistry, The Weizmann Institute of Science

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 11期

关键词：

D O I：

10.1021/jo00298a008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

: (Tri-rc-butyltin)thioimidoyl radicals of type 6, which were efficiently generated by treatment of alk-3-enyl-and alk-4-enylisothiocyanates with tri-n-butyltin hydride and AIBN, underwent exo cyclization to give, after hydrolysis, the corresponding 7- or 5-thiolactams in good to excellent yields. © 1990, American Chemical Society. All rights reserved.

引用

收藏

页码：3442 / 3444

页数：3

相关论文

共 30 条

[11]

CONVEY DJ, 1987, TETRAHEDRON LETT, V28, P5949

[12] CARBONYL RADICAL CYCLIZATIONS - PREPARATION OF SOME HETEROCYCLIC KETONES [J].

CRICH, D ;

EUSTACE, KA ;

RITCHIE, TJ .

HETEROCYCLES, 1989, 28 (01) :67-70

[13] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1. [J].

CURRAN, DP .

SYNTHESIS-STUTTGART, 1988, (06) :417-439

[14] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .2. [J].

CURRAN, DP .

SYNTHESIS-STUTTGART, 1988, (07) :489-513

[15] FORMATION OF CC BONDS BY ADDITION OF FREE-RADICALS TO ALKENES [J].

GIESE, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (10) :753-764

[16]

Giese B., 1986, RADICALS ORGANIC SYN

[17] SYNTHESIS OF CARBOCYCLES FROM OMEGA-SUBSTITUTED ALPHA,BETA-UNSATURATED ESTERS VIA RADICAL-INDUCED CYCLIZATIONS [J].

HANESSIAN, S ;

DHANOA, DS ;

BEAULIEU, PL .

CANADIAN JOURNAL OF CHEMISTRY, 1987, 65 (08) :1859-1866

[18] FREE-RADICAL CARBON-CARBON BOND FORMATION IN ORGANIC-SYNTHESIS [J].

HART, DJ .

SCIENCE, 1984, 223 (4639) :883-887

[19] TRIORGANOTIN HYDRIDE REDUCTION OF "6-BETA-ISOTHIOCYANATOPENICILLANATES - A RADICAL-INDUCED SULFUR-C(2) BOND-CLEAVAGE [J].

JOHN, DI ;

TYRRELL, ND ;

THOMAS, EJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (17) :901-902

[20] SYNTHESIS OF (ISOTHIOCYANATOACYL)AMINO ACIDS [J].

KRICHELDORF, HR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (07) :507-+