PREPARATION AND REACTIVITY OF METHYL 3,3-BIS(4-(DIMETHYLAMINO)PYRIDINIUM-1-YL)PROPENOATE DICHLORIDE

被引：12
|
作者：
KOCH, AS [1 ]
WATERMAN, KC [1 ]
BANKS, K [1 ]
STREITWIESER, A [1 ]
机构：
[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 25期
关键词：
D O I：
10.1021/jo00312a024
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The preparation, structure, and reactivity of methyl 3,3-bis(4-(dimethylamino)pyridinium-l-yl)propenoate dichloride (1) are discussed. 1 tetrachloride (2) was converted to 1 with formic or acetic acid in methanol. A mechanism for the conversion of 2 to 1 is suggested. Hydrolysis of 1 under basic conditions gave 3,3-bis(4-(dimethylamino)pyridinium-l-yl)propenoic acid (3), which has a pKa of 2. The X-ray structure of 1 shows that the pyridinium rings are both twisted with respect to the double bond; the resulting high steric hindrance prevent Diels-Alder reactions with dienes despite the electrophilic nature of the system. © 1990, American Chemical Society. All rights reserved.
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页码：6166 / 6171
页数：6
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