OXIDATION DURING REDUCTIVE CYCLIZATIONS USING BU3SNH

被引：113

作者：

BOWMAN, WR

HEANEY, H

JORDAN, BM

机构：

[1] Depanment of Chemistry, University of Technology, Loughborough,

来源：

TETRAHEDRON | 1991年 / 47卷 / 48期

关键词：

RADICAL CYCLIZATION; TRIBUTYLTIN HYDRIDE; SRN1; MECHANISM; RADICAL ANIONS; RADICALS;

D O I：

10.1016/S0040-4020(01)96061-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reductive cyclisations using Bu3SnH include an ''oxidation'' step if the removal of an acidic proton from the intermediate cyclised radical, by Bu3SnH acting as a base, is favourable. A ''pseudo S(RN1) mechanism is proposed.

引用

页码：10119 / 10128

页数：10

共 39 条

[1] CONSECUTIVE RING-CLOSURE AND NEOPHYL REARRANGEMENT OF SOME ALKENYLARYL RADICALS
ABEYWICKREMA, AN
BECKWITH, ALJ
GERBA, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) : 4072 - 4078
[2] CYCLIZATIONS OF ENE RADICALS - IMIDOYL RADICALS AS INTERMEDIATES IN THE SYNTHESIS OF HETEROCYCLIC-COMPOUNDS
BACHI, MD
DENENMARK, D
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) : 1886 - 1888
[3] CYCLISATIONS WITH HYDRAZINE .1. THE PREPARATION OF PHENANTHRENE COMPOUNDS AND OF PYRENE FROM ALDEHYDES - A VARIATION IN REDUCTIONS OF THE WOLFF-KISHNER TYPE
BACON, RGR
LINDSAY, WS
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1958, (APR): : 1375 - 1381
[4] MECHANISM OF CYCLIZATION OF ARYL RADICALS CONTAINING UNSATURATED ORTHO-SUBSTITUENTS
BECKWITH, ALJ
GARA, WB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1975, (07): : 795 - 802
[5] INTRAMOLECULAR AROMATIC-SUBSTITUTION (SRN1) REACTIONS - USE OF ENTRAINMENT FOR THE PREPARATION OF BENZOTHIAZOLES
BOWMAN, WR
HEANEY, H
SMITH, PHG
[J]. TETRAHEDRON LETTERS, 1982, 23 (48) : 5093 - 5096
[6] BUNNETT JF, 1961, J AM CHEM SOC, V83, P1694
[7] HOMOLYTIC SUBSTITUTION AT FURAN AND THIOPHENE - RATE CONSTANTS FOR THE FORMATION AND DECAY OF THE RADICAL INTERMEDIATES
BURKEY, TJ
GRILLER, D
LUNAZZI, L
NAZRAN, AS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (21) : 3704 - 3707
[8] RADICAL CHEMISTRY ASSOCIATED WITH THE THIOCARBONYL GROUP
CRICH, D
QUINTERO, L
[J]. CHEMICAL REVIEWS, 1989, 89 (07) : 1413 - 1432
[9] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1.
CURRAN, DP
[J]. SYNTHESIS-STUTTGART, 1988, (06): : 417 - 439
[10] ESTEVEZ JC, 1991, TETRAHEDRON LETT, V32, P539

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