THE POLYMERIZATION OF 3-METHY-N-(PHENYLSULFONYL)-1-AZA-1,3-BUTADIENE

被引:5
作者
BONNER, BA [1 ]
PADIAS, AB [1 ]
HALL, HK [1 ]
机构
[1] UNIV ARIZONA,DEPT CHEM,CS MARVEL LABS CHEM,TUCSON,AZ 85721
关键词
D O I
10.1007/BF00296041
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A study of the polymerizability of the first crystalline 1-azabutadiene carrying an electron-withdrawing group on nitrogen is described. A convenient one-step synthesis of 3-methyl-N-(phenylsulfonyl)-1-aza-1,3-butadiene (MPAB) from methacrolein and benzenesulfonamide using titanium tetrachloride and triethylamine led to a crystalline azabutadiene monomer in good yield. With anionic initiators the monomer readily oligomerized to materials in which MPAB has reacted in a 4,1-fashion. Under radical conditions the monomer did not homopolymerize, but did copolymerize with styrene monomers to polymers with molecular weights up to 10,000. These radical copolymerizations involved exclusive 4,3-propagation (vinyl) for the azadiene monomer.
引用
收藏
页码:517 / 523
页数:7
相关论文
共 7 条
[1]   INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF N-SULFONYL ALPHA,BETA-UNSATURATED IMINES - A GENERAL-APPROACH TO IMPLEMENTATION OF THE 4-PI PARTICIPATION OF 1-AZA-1,3-BUTADIENES IN DIELS-ALDER REACTIONS [J].
BOGER, DL ;
CORBETT, WL ;
CURRAN, TT ;
KASPER, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) :1713-1729
[2]  
BOGER DL, 1987, HETERO DIELSALDER ME
[3]  
HALL HK, 1992, IN PRESS MAKROMOL CH
[4]   NEW SYNTHESIS OF 2-AZETINES AND 1-AZABUTADIENES AND THE USE OF THE LATTER IN DIELS-ALDER REACTIONS - TOTAL SYNTHESIS OF (+/-)-DELTA-CONICEINE [J].
JUNG, ME ;
CHOI, YM .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6729-6730
[5]   SYNTHESIS AND POLYMERIZATION OF N-CARBETHOXY-3-METHYL-1-AZA-1,3-BUTADIENE [J].
KIM, JB ;
HALL, HK .
MACROMOLECULES, 1988, 21 (06) :1547-1552
[6]   SYNTHESIS AND POLYMERIZATION OF 1-AZABUTADIENE MONOMERS [J].
KITAYAMA, T ;
HALL, HK .
MACROMOLECULES, 1987, 20 (07) :1451-1455
[7]   THE N-ACYL-ALPHA-CYANO-1-AZADIENES - REMARKABLY REACTIVE HETERODIENES IN THE DIELS-ALDER REACTION [J].
TENG, M ;
FOWLER, FW .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) :5646-5653