HYDROLYSIS OF MUSTARD DERIVATIVES - REMARKABLE TOSYLATE CHLORIDE AND CHLORIDE DINITROPHENOLATE RATE RATIOS

被引:15
作者
MCMANUS, SP [1 ]
NEAMATIMAZREAH, N [1 ]
PALEY, MS [1 ]
HOVANES, BA [1 ]
HARRIS, JM [1 ]
机构
[1] UNIV ALABAMA,DEPT CHEM,HUNTSVILLE,AL 35899
关键词
D O I
10.1016/S0040-4039(00)98754-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:4571 / 4574
页数:4
相关论文
共 20 条
[11]   HYDROLYSIS OF MUSTARD DERIVATIVES - FAILURE OF THE RABER-HARRIS PROBE IN PREDICTING NUCLEOPHILIC ASSISTANCE [J].
MCMANUS, SP ;
NEAMATIMAZRAEH, N ;
HOVANES, BA ;
PALEY, MS ;
HARRIS, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (11) :3393-3395
[12]   CLASSICAL CARBONIUM-IONS .3. PREPARATION AND ACETOLYSIS OF SOME ALKYL 2,4-DINITROPHENYL ETHERS [J].
PAGE, ID ;
WHITING, MC ;
PRITT, JR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (07) :906-&
[13]   SOLVATION OF IONS .2. DIPOLAR APROTIC SOLVENTSAS MEDIA FOR NUCLEOPHILIC SUBSTITUTION REACTIONS AT A SATURATED CARBON ATOM [J].
PARKER, AJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1961, (MAR) :1328-&
[14]   CHEMICAL EFFECTS OF STERIC STRAINS .21. SOLVOLYSIS OF TERTIARY METHYL-BUTYLCARBINYL AND TERT-BUTYLCARBINYL P-NITROBENZOATES - EVIDENCE THAT STERIC EFFECTS ARE MORE IMPORTANT IN RIGID BICYCLIC SYSTEMS THAN IN ACYCLIC AND ALICYCLIC SYSTEMS [J].
PETERS, EN ;
BROWN, HC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (10) :2892-2895
[15]   ANALYSIS OF SWAIN-MOSELEY-BOWN EQUATION AND COMPARISON OF RESULTS WITH NUCLEOPHILICITIES DERIVED FROM HALONIUM ION REACTIONS [J].
PETERSON, PE ;
VIDRINE, DW ;
WALLER, FJ ;
HENRICHS, PM ;
MAGAHA, S ;
STEVENS, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (24) :7968-7976
[16]   CONTRASTING RESPONSES IN AQUEOUS TRIFLUOROETHANOL AND AQUEOUS ETHANOL AS A PROBE FOR NUCLEOPHILIC SOLVENT ASSISTANCE IN SOLVOLYSIS [J].
RABER, DJ ;
NEAL, WC ;
DUKES, MD ;
HARRIS, JM ;
MOUNT, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (26) :8137-8146
[17]   SN2-SN1 SPECTRUM .2. QUANTITATIVE TREATMENTS OF NUCLEOPHILIC SOLVENT ASSISTANCE - SCALE OF SOLVENT NUCLEOPHILICITIES [J].
SCHADT, FL ;
BENTLEY, TW ;
SCHLEYER, PV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (24) :7667-7674
[18]   CLASSICAL CARBONIUM IONS .2. SYNTHESIS, PROPERTIES, AND SOLVOLYSIS OF ALKYL PICRATES AND RELATED COMPOUNDS - COMPARISON OF ARENESULPHONATE AND PHENOXIDE LEAVING GROUPS [J].
SINNOTT, ML ;
WHITING, MC .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (05) :965-&
[19]   REMARKABLY LARGE SOLVOLYTIC RATE ENHANCEMENT DUE TO RELIEF OF GROUND-STATE LEAVING GROUP STRAIN [J].
SLUTSKY, J ;
BINGHAM, RC ;
SCHLEYER, PV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (06) :1969-1970
[20]   NEIGHBORING GROUP PARTICIPATION BY A PYRIDINE RING .2. EFFECTS OF AROMATIC SUBSTITUENTS ON SOLVOLYSIS OF 5,8-METHANO-5,6,7,8-TETRAHYDROISOQUINOLINE AND BENZONORBORNENE DERIVATIVES [J].
TANIDA, H ;
IRIE, T ;
HAYASHI, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (06) :821-825