DIASTEREOSELECTIVE FORMATION OF CYCLIC CARBONATES BY CYCLIZATION OF ALKENYLOXYCARBONYLOXY RADICALS

被引：42

作者：

BECKWITH, ALJ

DAVISON, IGE

机构：

[1] Research School of Chemistry, Australian National University, Canberra, ACT 2601

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 01期

关键词：

D O I：

10.1016/S0040-4039(00)71215-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alkenyloxycarbonyloxy radical (8) derived from trans-hex-2-en-l-ol via the N-hydroxypyridine-2-thione carbonate (4) undergoes fast (k(c) > 4.0 x 10(8) s-1 at 80-degrees-C) cyclization exclusively in the exo mode to give a cyclic radical (9) which is converted into products (6,7) by diastereoselective S(H)2 reactions; radicals derived from homoallylic alcohols behave similarly.

引用

页码：49 / 52

页数：4

共 24 条

[1] THE INVENTION OF NEW RADICAL CHAIN REACTIONS .8. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS - A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC-ACIDS
BARTON, DHR
CRICH, D
MOTHERWELL, WB
[J]. TETRAHEDRON, 1985, 41 (19) : 3901 - 3924
[2] THE INVENTION OF RADICAL REACTIONS .15. SOME MECHANISTIC ASPECTS OF THE DECARBOXYLATIVE REARRANGEMENT OF THIOHYDROXAMIC ESTERS
BARTON, DHR
BRIDON, D
FERNANDEZPICOT, I
ZARD, SZ
[J]. TETRAHEDRON, 1987, 43 (12) : 2733 - 2740
[3] BECKWITH AL, 1974, TETRAHEDRON LETT, P2251
[4] GENERATION OF ALKOXY RADICALS FROM N-ALKOXYPYRIDINETHIONES
BECKWITH, ALJ
HAY, BP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (13) : 4415 - 4416
[5] STEREOSELECTIVITY OF RING-CLOSURE OF SUBSTITUTED HEX-5-ENYL RADICALS
BECKWITH, ALJ
LAWRENCE, T
SERELIS, AK
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (11) : 484 - 485
[6] SOME GUIDELINES FOR RADICAL REACTIONS
BECKWITH, ALJ
EASTON, CJ
SERELIS, AK
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (11) : 482 - 483
[7] KINETICS OF THE REVERSIBLE BETA-SCISSION OF THE CYCLOPENTYLOXY RADICAL
BECKWITH, ALJ
HAY, BP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (01) : 230 - 234
[8] BECKWITH ALJ, 1989, J ORG CHEM, V54, P4330
[9] BECKWITH ALJ, 1981, TETRAHEDRON, V37, P3071
[10] BECKWITH ALJ, UNPUB

← 1 2 3 →