Cyclization of methyl-substituted 6-heptenyl radicals

被引：17

作者：

Bailey, WF ^{[1
]}

Longstaff, SC ^{[1
]}

机构：

[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 14期

关键词：

D O I：

10.1021/ol0160755

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The behavior of a series of methyl-substituted 6-heptenyl radicals, generated from the corresponding iodides ((Me(3)Si)(3)SiH, AlBN in benzene at 80 degreesC), has been investigated. The stereoselectivity of the B-exo cyclizations, affording dimethylcyclohexanes, is low, and sizable quantities of methylcycloheptane, generated via 7-endo cyclization, are also produced.

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页码：2217 / 2219

页数：3

相关论文

共 29 条

[1] SYNTHESIS OF ENANTIOMERICALLY PURE GEM-DIFLUOROCYCLOHEXANE DERIVATIVES BY INTRAMOLECULAR TRAPPING OF ALPHA,ALPHA-DIFLUOROALKYL RADICALS [J].

ARNONE, A ;

BRAVO, P ;

FRIGERIO, M ;

VIANI, F ;

CAVICCHIO, G ;

CRUCIANELLI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3459-3466

[2]

BECKWITH AL, 1974, TETRAHEDRON LETT, P2251

[3] STEREOSELECTIVITY OF RING-CLOSURE OF SUBSTITUTED HEX-5-ENYL RADICALS [J].

BECKWITH, ALJ ;

LAWRENCE, T ;

SERELIS, AK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (11) :484-485

[4] SOME GUIDELINES FOR RADICAL REACTIONS [J].

BECKWITH, ALJ ;

EASTON, CJ ;

SERELIS, AK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (11) :482-483

[5] A FORCE-FIELD STUDY OF ALKENYL RADICAL RING-CLOSURE [J].

BECKWITH, ALJ ;

SCHIESSER, CH .

TETRAHEDRON LETTERS, 1985, 26 (03) :373-376

[6] REGIO-SELECTIVITY AND STEREO-SELECTIVITY IN RADICAL REACTIONS [J].

BECKWITH, ALJ .

TETRAHEDRON, 1981, 37 (18) :3073-3100

[7]

BECKWITH ALJ, 1980, REARRANGEMENTS GROUN, V1

[8] Intramolecular Addition In Hex-5-enyl, Hept-6-enyl, and Oct-7-enyl Radicals [J].

Beckwith, Athelstan L. J. ;

Moad, Graeme .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (12) :472-473

[9] FURTHER OBSERVATIONS ON THE THERMAL-STABILITY OF N-HYDROXY-2-THIOPYRIDONE ESTERS - IMPROVED DECARBOXYLATIVE RADICAL ADDITIONS TO OLEFINS [J].

BOIVIN, J ;

CREPON, E ;

ZARD, SZ .

TETRAHEDRON LETTERS, 1991, 32 (02) :199-202

[10] RATE CONSTANTS AND ARRHENIUS PARAMETERS FOR THE REACTIONS OF PRIMARY, SECONDARY, AND TERTIARY ALKYL RADICALS WITH TRI-NORMAL-BUTYLTIN HYDRIDE [J].

CHATGILIALOGLU, C ;

INGOLD, KU ;

SCAIANO, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (26) :7739-7742