CHAIN TRANSFER ACTIVITY OF SOME ACTIVATED ALLYLIC COMPOUNDS

被引:89
作者
MEIJS, GF [1 ]
RIZZARDO, E [1 ]
THANG, SH [1 ]
机构
[1] CSIRO,DIV CHEM & POLYMERS,PRIVATE BAG 10,CLAYTON,VIC 3168,AUSTRALIA
关键词
Allylic Compounds - Chain Transfer Agents - Homolytic Leaving Group - Radical Polymerization;
D O I
10.1007/BF00395571
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Various olefins that are activated towards free radical addition and contain a homolytic leaving group in the allylic position are effective chain transfer agents in free radical polymerizations of methyl methacrylate and other monomers. These allylic compounds include bromides, phosphonates, stannanes, thioethers, sulfoxides, and sulfones. Allylic silanes and chlorides, however, do not posess significant chain transfer activity. Suitable activating substituents towards radical addition are phenyl, ethoxycarbonyl, cyano, and acetoxy. Several of the compounds have an advantage over thiols in that they do not contain sulfur. © 1990 Springer-Verlag.
引用
收藏
页码:501 / 505
页数:5
相关论文
共 13 条
[1]   ELIMINATION-ADDITION .14. ADDITION OF CARBOXYLATE IONS TO ALLENES AND ACETYLENES AND USE OF ADDUCTS IN ACYLATION [J].
APPLEYARD, GD ;
STIRLING, CJ .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (24) :2686-+
[2]  
BALDWIN JE, 1986, J CHEM SOC CHEM COMM
[3]   CARBETHOXYALLYLATION USING RADICAL CHEMISTRY [J].
BARTON, DHR ;
CRICH, D .
TETRAHEDRON LETTERS, 1984, 25 (26) :2787-2790
[4]  
HAIDER A, 1985, SYNTHESIS-STUTTGART, P271
[5]   STUDIES OF SULFINYL RADICALS .2. REVERSIBILITY OF ADDITION TO STYRENE [J].
IINO, M ;
MATSUDA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (18) :3108-3109
[6]   A NEW-ONE-ELECTRON-CARBON-CARBON BOND FORMING REACTION - SEPARATION OF THE CHAIN PROPAGATION STEPS IN FREE-RADICAL ALLYLATION [J].
KECK, GE ;
BYERS, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5442-5444
[7]   REACTIVITY OF ALLYLIC AND VINYLIC SILANES, GERMANES, STANNANES AND PLUMBANES TOWARD SH2' OR SH2 SUBSTITUTION BY CARBON-CENTERED OR HETEROATOM-CENTERED FREE-RADICALS [J].
LIGHT, JP ;
RIDENOUR, M ;
BEARD, L ;
HERSHBERGER, JW .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 326 (01) :17-24
[8]   PREPARATION OF CONTROLLED MOLECULAR-WEIGHT, OLEFIN-TERMINATED POLYMERS BY FREE-RADICAL METHODS - CHAIN TRANSFER USING ALLYLIC SULFIDES [J].
MEIJS, GF ;
RIZZARDO, E ;
THANG, SH .
MACROMOLECULES, 1988, 21 (10) :3122-3124
[9]   STUDIES OF SULFINYL RADICALS .1. THERMAL DECOMPOSITIONS OF BENZHYDRYL PARA-TOLYL SULFOXIDE AND BENZHYDRYL METHYL SULFOXIDE [J].
MIZUNO, H ;
MATSUDA, M ;
IINO, M .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (03) :520-525
[10]  
PINES H, 1957, J ORG CHEM, V22, P113