Formation of some oxygen-containing heterocycles by radical cyclization: The stereochemical influence of anomeric effects

被引：26

作者：

Beckwith, ALJ ^{[1
]}

Page, DM

机构：

[1] Australian Natl Univ, Res Sch Chem, Canberra, ACT 0200, Australia

[2] Australian Natl Univ, Dept Chem, Canberra, ACT 0200, Australia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 15期

关键词：

D O I：

10.1021/jo980359u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The influence of the anomeric effect on radical cyclization has been examined by determining the stereochemical outcome of the ring closure of 10 suitably substituted radicals. The stereochemistry of the products formed from the acyclic precursors 4a-f indicates that for suitably constituted radicals anomeric interactions stabilize pseudoaxially substituted transition structures 14 thus affording products with stereochemistry the reverse of that normally observed.

引用

页码：5144 / 5153

页数：10

共 77 条

[1] ALEXANIAN V, 1978, TETRAHEDRON LETT, V46, P4475
[2] [Anonymous], 1993, ANOMERIC EFFECT ASS
[3] Armarego W.L. F., 1996, PURIFICATION LAB CHE, V4th
[4] MULTIPLE RADICAL ADDITIONS - AN EXPEDIENT ENTRY INTO COMPLEX FRAMEWORKS
BARTON, DHR
DASILVA, E
ZARD, SZ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (04) : 285 - 287
[5] 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
[6] Beckwith A. L. J., 1980, REARRANGEMENTS GROUN, VI, P161, DOI [10.1016/B9780-12-481301-4.50010-3, DOI 10.1016/B9780-12-481301-4.50010-3]
[7] PREFERENTIAL CIS CYCLIZATION OF 6-HEPTEN-2-YL AND RELATED RADICALS - EXAMPLE OF ORBITAL SYMMETRY CONTROL
BECKWITH, AL
BLAIR, I
PHILLIPO.G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (05) : 1613 - 1614
[8] FORMATION OF SOME BICYCLIC AND TRICYCLIC SYSTEMS BY RADICAL RING-CLOSURE
BECKWITH, ALJ
ROBERTS, DH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) : 5893 - 5901
[9] THIOL-OXYGEN CO-OXIDATION REACTIONS OF CYCLOPENTENE, CIS-BUT-2-ENE AND TRANS-BUT-2-ENE, NORBORNENE, AND NORBORNADIENE
BECKWITH, ALJ
WAGNER, RD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (18) : 3638 - 3645
[10] 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

← 1 2 3 4 5 6 7 8 →