RADICAL CYCLIZATION REACTIONS - CYCLOPROPANE RING FORMATION BY 3-EXO-CYCLIZATION OF 5-PHENYLTHIO-3-PENTENYL RADICALS

被引：21

作者：

CEKOVIC, Z ^{[1
]}

SAICIC, R ^{[1
]}

机构：

[1] INST CHEM TECHNOL & MET,BELGRADE,YUGOSLAVIA

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(00)98035-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Free radical cyclopropane ring closure was accomplished by thermal decomposition of thiohydroxamic esters of 6-phenylthio-4-hexencic acids. When the reaction was performed in the presence of acrylonitrile; an addition/cyclization/elimination process took place and the corresponding cyclopentanecarbonitriles were obtained. © 1990.

引用

页码：6085 / 6088

页数：4

共 23 条

[1] THE INVENTION OF RADICAL REACTIONS .15. SOME MECHANISTIC ASPECTS OF THE DECARBOXYLATIVE REARRANGEMENT OF THIOHYDROXAMIC ESTERS
BARTON, DHR
BRIDON, D
FERNANDEZPICOT, I
ZARD, SZ
[J]. TETRAHEDRON, 1987, 43 (12) : 2733 - 2740
[2] THE INVENTION OF RADICAL CHAIN-REACTIONS .14. A DECARBOXYLATIVE RADICAL-ADDITION TO QUINONES
BARTON, DHR
BRIDON, D
ZARD, SZ
[J]. TETRAHEDRON, 1987, 43 (22) : 5307 - 5314
[3] KINETICS AND MECHANISM OF SOME VINYL RADICAL CYCLIZATIONS
BECKWITH, ALJ
OSHEA, DM
[J]. TETRAHEDRON LETTERS, 1986, 27 (38) : 4525 - 4528
[4] STEREOCHEMISTRY OF FREE-RADICAL ELIMINATIONS ON BETA-PHENYLTHIO RADICALS
BOOTHE, TE
GREENE, JL
SHEVLIN, PB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (04) : 951 - 956
[5] BURY A, 1982, J CHEM SOC P1, P345
[6] FREE-RADICAL ANNULATION OF CYCLOPENTANE RING
CEKOVIC, Z
SAICIC, R
[J]. TETRAHEDRON LETTERS, 1986, 27 (48) : 5893 - 5896
[7] RATE CONSTANTS AND ARRHENIUS PARAMETERS FOR THE REACTIONS OF PRIMARY, SECONDARY, AND TERTIARY ALKYL RADICALS WITH TRI-NORMAL-BUTYLTIN HYDRIDE
CHATGILIALOGLU, C
INGOLD, KU
SCAIANO, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (26) : 7739 - 7742
[8] A NEW TRI-NORMAL-BUTYLTIN HYDRIDE BASED REARRANGEMENT OF BROMOMETHYL BETA-KETO-ESTERS - A SYNTHETICALLY USEFUL RING EXPANSION TO GAMMA-KETO ESTERS
DOWD, P
CHOI, SC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) : 3493 - 3494
[9] NOVEL FREE-RADICAL RING-EXPANSION REACTIONS
DOWD, P
CHOI, SC
[J]. TETRAHEDRON, 1989, 45 (01) : 77 - 90
[10] EFFIO A, 1980, J AM CHEM SOC, V102, P1734, DOI 10.1021/ja00525a051

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