THE REGIOCHEMISTRY OF THE RADICAL-ADDITION OF N-CHLOROAMIDES TO ENOL ETHERS

被引:7
作者
CARON, G [1 ]
LESSARD, J [1 ]
机构
[1] UNIV SHERBROOKE,DEPT CHIM,SHERBROOKE J1K 2R1,QUEBEC,CANADA
关键词
D O I
10.1016/S0040-4020(01)88026-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The orientation of the radical addition of N-chloroamides (ZCONHCl) to enol ethers was studied as a function of Z and the enol ether structure and compared with the orientation of radical addition of thioacetic acid and the orientation of typical electrophilic additions.
引用
收藏
页码:8039 / 8058
页数:20
相关论文
共 37 条
  • [1] N-MONOCHLORINATION AND N-MONOBROMINATION OF CARBAMATES AND CARBOXAMIDES BY SODIUM-HYPOCHLORITE AND HYPOBROMITE
    BACHAND, C
    DRIGUEZ, H
    PATON, JM
    TOUCHARD, D
    LESSARD, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (21) : 3136 - 3138
  • [2] BALABAN AT, 1971, REV ROUM CHIM, V16, P725
  • [3] STABLE FREE-RADICALS .1. NEW PRINCIPLE GOVERNING STABILITY OF ORGANIC FREE-RADICALS
    BALDOCK, RW
    HUDSON, P
    KATRITZKY, AR
    SOTI, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (12): : 1422 - 1427
  • [4] ORTHOAMIDES .12. SYNTHESIS OF ACYL ISOCYANATE O,N-ACETALS OR -N,N-ACETALS FROM AMIDE ACETALS OR FROM AN AMINAL TERT BUTYLESTER AND N-HALOGENCARBONAMIDES, HALOGEN UREAS AND N-CHLOROURETHANES
    BREDERECK, H
    SIMCHEN, G
    PORKERT, H
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1970, 103 (01): : 245 - +
  • [5] SYNTHESIS OF TRISUBSTITUTED ENOL ETHERS AND OF METHYL KETONES FROM KETONES
    CARON, G
    LESSARD, J
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1973, 51 (06): : 981 - 983
  • [6] CHONG R, 1966, TETRAHEDRON LETT, P741
  • [7] COTTRELL TL, 1958, STRENGTHS CHEM BONDS, P273
  • [8] CHROMOUS CHLORIDE PROMOTED ADDITION OF N-HALOAMIDES TO OLEFINS .3. SCOPE AND LIMITATIONS FOR SYNTHESIS OF N-(2-HALOALKYL)AMIDES
    DRIGUEZ, H
    PATON, JM
    LESSARD, J
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (04): : 700 - 719
  • [9] CHROMOUS CHLORIDE PROMOTED ADDITION OF N-HALOAMIDES TO OLEFINS .4. MECHANISTIC ASPECTS
    DRIGUEZ, H
    LESSARD, J
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (04): : 720 - 732
  • [10] CHROMOUS CHLORIDE PROMOTED ADDITION OF N-HALOAMIDES TO OLEFINS .5. ADDITION OF N-CHLOROAMIDES TO ENOL ETHERS - SYNTHESIS OF ACYLOXY AND ACYL DERIVATIVES OF ALPHA-AMINO ACETALS AND KETALS (ALDEHYDES AND KETONES) AND OF 2-AMINO SUGARS
    DRIGUEZ, H
    VERMES, JP
    LESSARD, J
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1978, 56 (01): : 119 - 130