RADICAL CYCLIZATIONS OF BROMO ACYLSILANES AND INTRAMOLECULAR TRAPPING OF THE REARRANGED ALPHA-SILYLOXY RADICALS

被引：30

作者：

TSAI, YM

TANG, KH

JIAANG, WT

机构：

[1] Department of Chemistry, National Taiwan University, Taipei

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 08期

关键词：

ACYLSILANE; TANDEM RADICAL CYCLIZATION; 1,5-HYDROGEN ATOM TRANSFER; RADICAL BROOK REARRANGEMENT;

D O I：

10.1016/S0040-4039(00)91780-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Radical 1,5-exo cyclizations of acylsilanes involving secondary radicals are quite effective. In contrast, 1,6-exo cyclizations are more sensitive toward steric effect. Tandem radical cyclization process can be designed.

引用

页码：1303 / 1306

页数：4

共 16 条

[1] STEREOCHEMISTRY OF THE REVERSIBLE CYCLIZATION OF OMEGA-FORMYLALKYL RADICALS
BECKWITH, ALJ
RANER, KD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (18) : 4954 - 4962
[2] PHOTOREDUCTIVE CYCLIZATION OF DELTA,EPSILON-UNSATURATED KETONES
BELOTTI, D
COSSY, J
PETE, JP
PORTELLA, C
[J]. TETRAHEDRON LETTERS, 1985, 26 (38) : 4591 - 4594
[3] SYNTHESIS OF BICYCLIC CYCLOPENTANOLS BY PHOTOREDUCTIVE CYCLIZATION OF DELTA,EPSILON-UNSATURATED KETONES
BELOTTI, D
COSSY, J
PETE, JP
PORTELLA, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (22) : 4196 - 4200
[4] CURRAN DP, 1992, SYNLETT, P631
[5] UNSATURATED ACYLGERMANES ISOMERIZE BY A CHAIN MECHANISM INVOLVING RADICAL CYCLIZATION TO THE CARBONYL GROUP OF AN ACYLGERMANE
CURRAN, DP
LIU, HT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) : 3463 - 3465
[6] INTRAMOLECULAR HYDROGEN TRANSFER-REACTIONS OF ORTHO-(BROMOPHENYL)DIALKYLSILYL ETHERS - PREPARATION OF RAPAMYCIN-D1
CURRAN, DP
SOMAYAJULA, KV
YU, HS
[J]. TETRAHEDRON LETTERS, 1992, 33 (17) : 2295 - 2298
[7] MECHANISTIC PHOTOCHEMISTRY OF ACYLSILANES .2. REACTION WITH ELECTRON-POOR OLEFINS
DALTON, JC
BOURQUE, RA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (03) : 699 - 700
[8] DIISOBUTYLALUMINUM "2,6-DI-TERT-BUTYL-4-METHYLPHENOXIDE - NOVEL STEREOSELECTIVE REDUCING AGENT FOR PROSTAGLANDIN SYNTHESIS
IGUCHI, S
NAKAI, H
HAYASHI, M
YAMAMOTO, H
MARUOKA, K
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (10) : 3033 - 3041
[9] REDUCTIVE TANDEM CYCLIZATION OF ALLYL PENTENYL KETONES
KARIVMILLER, E
MAEDA, H
LOMBARDO, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) : 4022 - 4024
[10] ELECTROREDUCTIVE CYCLIZATION - KETONES AND ALDEHYDES TETHERED TO ALPHA,BETA-UNSATURATED ESTERS (NITRILES) - FUNDAMENTAL INVESTIGATIONS
LITTLE, RD
FOX, DP
VANHIJFTE, L
DANNECKER, R
SOWELL, G
WOLIN, RL
MOENS, L
BAIZER, MM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) : 2287 - 2294

← 1 2 →