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
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.
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页码:1353 / 1366
页数:14
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