METAL-ION EFFECTS ON THE RATE OF INTRAMOLECULAR O-ALKYLATION OF THE ANION OF ETHYL(3-CHLOROPROPYL)ACETOACETATE

被引：8

作者：

CACCIAPAGLIA, R

MANDOLINI, L

机构：

[1] UNIV ROMA LA SAPIENZA,CNR,CTR STUDI MECCAN REAZ,I-00185 ROME,ITALY

[2] UNIV ROMA LA SAPIENZA,DEPARTIMENTO CHIM,I-00185 ROME,ITALY

来源：

TETRAHEDRON | 1990年 / 46卷 / 04期

关键词：

D O I：

10.1016/S0040-4020(01)86699-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The retarding effect of alkali metal and alkaline-earth metal ions on the rate of intramolecular O-alkylation of the title compound has been thoroughly investigated in 99% aqueous Me2SO at 25° C. Rate data have been dissected into contributions of free ions (ki) and ion pairs (kip). Comparison of the present results with available data for intramolecular C-alkylation of a strictly related system, reveals that rate-depressing effects due to cation pairing turn out to be remarkably similar in the two processes, which is at variance with the expectation of a more pronounced cation dependence of the kip/ki ratios for O-alkylation than for C-alkylation. © 1990.

引用

页码：1353 / 1366

页数：14

共 15 条

[1]

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[2]

ARNETT EM, 1987, GAZZ CHIM ITAL, V117, P237

[3] ION-PAIRING AND REACTIVITY OF ENOLATE ANIONS .6. KINETICS AND THERMODYNAMICS FOR REACTION OF ALKALI ACETYLACETONATES WITH ALKYL-HALIDES IN DIMETHYL-SULFOXIDE [J].