ACYL RADICAL CYCLIZATIONS IN SYNTHESIS .5. FURTHER TANDEM PROCESSES - FORMATION OF AN ALPHA-METHYLENECYCLOHEXANONE BY A CYCLIZATION-FRAGMENTATION HYDROGEN-ABSTRACTION SEQUENCE

被引：26

作者：

BATTY, D ^{[1
]}

CRICH, D ^{[1
]}

机构：

[1] UNIV ILLINOIS,DEPT CHEM,M-C 111,BOX 4348,CHICAGO,IL 60680

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 23期

关键词：

D O I：

10.1039/p19920003205

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two Se-phenyl 7-cyclopropyl(selenohept-6-enoate) esters were prepared and their reactions with tributylstannane and a free-radical initiator were studied. In both cases the initial acyl radical cyclization proceeded smoothly to give cyclopropylmethyl radicals which then suffered clean ring opening to homoallylic radicals. In the case of the initial substrate carrying a phenyl group at the 7-position a further radical rearrangement involving delta-hydrogen abstraction occurred to give, after chain transfer with the stannane, an alpha-alkylidenecyclohexanone.

引用

页码：3205 / 3209

页数：5

共 50 条

[1] FREE-RADICAL SELENOSULFONATION OF VINYLCYCLOPROPANES, A CYCLOPROPYLIDENE, AND CYCLOPROPYLACETYLENE - RELATIVE RATES OF CHAIN-TRANSFER, RING-OPENING, AND INVERSION IN RADICAL INTERMEDIATES [J].

BACK, TG ;

MURALIDHARAN, KR .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (01) :121-125

[2] CARBOCYCLIC RING EXPANSION REACTIONS VIA FREE-RADICAL PATHWAYS .3. [J].

BALDWIN, JE ;

ADLINGTON, RM ;

SINGH, R .

TETRAHEDRON, 1992, 48 (16) :3385-3412

[3] CARBOCYCLIC RING EXPANSION REACTIONS VIA RADICAL CHAIN PROCESSES .2. [J].

BALDWIN, JE ;

ADLINGTON, RM ;

ROBERTSON, J .

TETRAHEDRON, 1991, 47 (33) :6795-6812

[4] CARBOCYCLIC RING EXPANSION REACTIONS VIA RADICAL CHAIN PROCESSES [J].

BALDWIN, JE ;

ADLINGTON, RM ;

ROBERTSON, J .

TETRAHEDRON, 1989, 45 (04) :909-922

[5]

BATTY D, 1990, SYNTHESIS-STUTTGART, P273

[6]

Beckwith A. L. J., 1980, REARRANGEMENTS GROUN, V1, P162

[7] REARRANGEMENT OF SUITABLY CONSTITUTED ARYL, ALKYL, OR VINYL RADICALS BY ACYL OR CYANO GROUP MIGRATION [J].

BECKWITH, ALJ ;

OSHEA, DM ;

WESTWOOD, SW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2565-2575

[8] GENERATION OF ALKOXY RADICALS FROM N-ALKOXYPYRIDINETHIONES [J].

BECKWITH, ALJ ;

HAY, BP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (13) :4415-4416

[9] RING-CLOSURE OF THE 6-METHYLENECYCLODECYL RADICAL [J].

BECKWITH, ALJ ;

BOWRY, VW ;

SCHIESSER, CH .

TETRAHEDRON, 1991, 47 (01) :121-130

[10] BETA-FISSION OF 9-DECALINOXYL RADICALS - REVERSIBLE FORMATION OF 6-KETOCYCLODECYL RADICAL [J].

BECKWITH, ALJ ;

KAZLAUSKAS, R ;

SYNERLYONS, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (24) :4718-4722

← 1 2 3 4 5 →