Low-temperature preparations of unimolecular nitroxide initiators for ''living'' free radical polymerizations

被引：78

作者：

Braslau, R

Burrill, LC

Siano, M

Naik, N

Howden, RK

Mahal, LK

机构：

[1] Dept. of Chemistry and Biochemistry, University of California, Santa Cruz

来源：

MACROMOLECULES | 1997年 / 30卷 / 21期

关键词：

D O I：

10.1021/ma970822p

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Low-temperature methods for the preparation of monomeric initiators for use in ''living'' free radical olefin polymerizations have been developed. Oxidative methods for generating carbon radicals in the presence of nitroxide traps such as TEMPO utilize PbO2 with benzylic, alkyl, or phenylhydrazines or CuCl2 with lithium enolates. Photolytic methods employ [Cp(CO)(2)Fe](2) with a benzylic bromide, diphenyl disulfide with styrene, or di-tert-butyl peroxide with ethers. The use of di-tert-butyl hyponitrite with ethers generates carbon radicals at 50 degrees C that are trapped by TEMPO.

引用

页码：6445 / 6450

页数：6

共 39 条

[1] RATE CONSTANTS FOR TERMINATION AND TEMPO TRAPPING OF SOME RESONANCE STABILIZED HYDROAROMATIC RADICALS IN THE LIQUID-PHASE
ARENDS, IWCE
MULDER, P
CLARK, KB
WAYNER, DDM
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1995, 99 (20) : 8182 - 8189
[2] KINETICS OF NITROXIDE RADICAL TRAPPING .1. SOLVENT EFFECTS
BECKWITH, ALJ
BOWRY, VW
INGOLD, KU
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) : 4983 - 4992
[3] A totally radical approach to the control of stereochemistry: Coupling of prochiral radicals with chiral nitroxyl radicals
Braslau, R
Burrill, LC
Mahal, LK
Wedeking, T
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (03): : 237 - 238
[4] GENERATION AND TRAPPING OF BENZYL RADICALS FROM BENZYL IODIDES BY COBALOXIME-MEDIATED IODINE ATOM ABSTRACTIONS
BROWN, TM
COOKSEY, CJ
CRICH, D
DRONSFIELD, AT
ELLIS, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (17): : 2131 - 2136
[5] THE STRUCTURES OF THE FREE-RADICAL SCAVENGER 1,1,3,3-TETRAMETHYLISOINDOLIN-2-YLOXYL, AND OF THE ALKOXY AMINE DERIVATIVE 5-(1,1,3,3-TETRAMETHYLISOINDOLIN-2-YLOXY)-1-VINYLPYRROLIDIN-2-ONE
BUSFIELD, WK
ENGELHARDT, LM
HEALY, PC
JENKINS, ID
THANG, SH
WHITE, AH
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1986, 39 (02) : 357 - 365
[6] THE T-BUTYLTHIYL RADICAL AS INITIATOR IN VINYLPOLYMERIZATIONS - INVESTIGATIONS INTO THE INITIATION STEP BY THE AMINOXYL TRAPPING TECHNIQUE
BUSFIELD, WK
HEILAND, K
JENKINS, ID
[J]. TETRAHEDRON LETTERS, 1994, 35 (35) : 6541 - 6542
[7] REACTION OF TERT-BUTOXY RADICALS WITH CYCLIC ALKENES STUDIED BY THE NITROXIDE RADICAL-TRAPPING TECHNIQUE
BUSFIELD, WK
GRICE, DI
JENKINS, ID
THANG, SH
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (10) : 1407 - 1415
[8] PHENYL THIYL RADICAL AS INITIATOR IN VINYL POLYMERIZATIONS - INVESTIGATIONS INTO THE INITIATION STEP BY THE AMINOXYL TRAPPING TECHNIQUE
BUSFIELD, WK
HEILAND, K
JENKINS, ID
[J]. TETRAHEDRON LETTERS, 1995, 36 (07) : 1109 - 1112
[9] SLOW NITROGEN INVERSION-N-O ROTATION IN 2-ALKOXY-1,1,3,3-TETRAMETHYLISOINDOLINES
BUSFIELD, WK
JENKINS, ID
THANG, SH
MOAD, G
RIZZARDO, E
SOLOMON, DH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (18) : 1249 - 1250
[10] UNEXPECTED DEOXYGENATION OF 2,2,6,6-TETRAMETHYLPIPERIDINE-1-OXYL (TEMPO) BY THIYL RADICALS THROUGH THE FORMATION OF ARYLSULPHINYL RADICALS
CARLONI, P
DAMIANI, E
IACUSSI, M
GRECI, L
STIPA, P
CAUZI, D
RIZZOLI, C
SGARABOTTO, P
[J]. TETRAHEDRON, 1995, 51 (45) : 12445 - 12452

← 1 2 3 4 →