ELIMINATION-REACTIONS OF (E)-O-P-NITROPHENYL-2,4-DINITROBENZALDOXIME PROMOTED BY TRIETHYLAMINE IN MECN-H2O

被引:12
作者
CHO, BR
YOON, COM
SONG, KS
机构
[1] Department of Chemistry, Korea University 1-Anamdong, Seoul
关键词
D O I
10.1016/0040-4039(95)00510-J
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Elimination reactions of (E)-O-p-nitrophenyl-2,4-dinitrobenzaldoxime promoted by triethylamine in MeCN-H2O proceeded by the E2 mechanism. The rate decreased as the mole % of MeCN increased up to 70% and then increased upon further increase in the MeCN concentration. The results have been interpreted with the solvent effect.
引用
收藏
页码:3193 / 3196
页数:4
相关论文
共 13 条
[1]   ELIMINATIONS FROM (E)-O-ARYLBENZALDEHYDE OXIMES PROMOTED BY HYDROXIDE IN 60-PERCENT-AQ DIMETHYL-SULFOXIDE - MECHANISM AND TRANSITION-STATE CHARACTERISTICS OF NITRILE-FORMING ELIMINATIONS [J].
CHO, BR ;
LEE, JC ;
CHO, NS ;
KIM, KD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (05) :489-492
[2]   ELIMINATIONS FROM (E)-O-ARYLBENZALDOXIMES PROMOTED BY TERTIARY-AMINES IN ACETONITRILE - EFFECTS OF ARYL SUBSTITUENTS, BASE STRENGTH, AND LEAVING GROUP UPON THE NITRILE-FORMING TRANSITION-STATE [J].
CHO, BR ;
KIM, KD ;
LEE, JC ;
CHO, NS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6145-6148
[3]   REACTION OF (E)-O-ARYLBENZALDOXIMES WITH SODIUM METHOXIDE IN METHANOL - EFFECT OF LEAVING GROUP UPON NITRILE-FORMING TRANSITION-STATE [J].
CHO, BR ;
JUNG, J ;
AHN, EK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (09) :3425-3429
[4]   REACTIONS OF (E)-O-ARYLBENZALDOXIMES WITH SECONDARY-AMINES IN ACETONITRILE - EFFECT OF BETA-ARYL SUBSTITUENTS UPON THE COMPETITION BETWEEN E2 AND SNAR REACTIONS [J].
CHO, BR ;
JE, JT .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23) :6190-6193
[5]   REACTIONS OF (E)-O-ARYLBENZALDOXIMES WITH SECONDARY-AMINES IN ACETONITRILE - COMPETITION BETWEEN E2 AND SNAR REACTIONS [J].
CHO, BR ;
MIN, BK ;
LEE, CW ;
JE, JT .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5513-5517
[6]  
COETZEE JF, 1965, PROG PHYS ORG CHEM, V4, P45
[7]   ELECTRONIC EFFECTS IN ELIMINATION REACTIONS .7. SNY AND ANTI ELIMINATIONS OF 3-PHENYL-2-NORBORNYL TOSYLATES [J].
DEPUY, CH ;
NAYLOR, CG ;
BECKMAN, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (08) :2750-&
[8]   MECHANISMS OF ELIMINATION-REACTIONS .39. STERIC AND ELECTRONIC EFFECTS ON STEREOCHEMISTRY IN ELIMINATIONS FROM PRIMARY ALKYLTRIMETHYLAMMONIUM SALTS [J].
DOHNER, BR ;
SAUNDERS, WH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (02) :245-247
[9]  
GANDLER JR, 1989, CHEM DOUBLE BONDED F, V2, P734
[10]   NITRILE-FORMING ELIMINATIONS FROM OXIME ETHERS [J].
HEGARTY, AF ;
TUOHEY, PJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1980, (09) :1313-1317