Product analysis, rate data, and effective molarity (e.m.) values have been obtained for the formation of catechol polymethylene ethers by the intramolecular alkylation of o-ω-bromoalkoxyphenoxides in Me 2SO-water (99 : 1, v/v). Twelve ring sizes were investigated in the range 6-32. Comparison with similar data for the reaction in EtOH-water (75 : 25, v/v) (except for n 32) showed that the e.m. values are largely independent of solvent despite the large solvent effect observed in both the cyclization reaction and the related intermolecular model reaction. Small effects only were observed in the medium ring region. The main possible factors playing a role in solvent effects on intramolecular cyclization have been critically analysed in the light of the data.
Ring-Closure Reactions. Part 15. Solvent Effects on Cyclic Aralkyl Ether Formation by Intramolecular Williamson Synthesis" / DALLA CORT, Antonella; Gabriello, Illuminati; Mandolini, Luigi; Bernardo, Masci. - In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS II. - ISSN 0300-9580. - STAMPA. - (1980), pp. 1774-1777.
Ring-Closure Reactions. Part 15. Solvent Effects on Cyclic Aralkyl Ether Formation by Intramolecular Williamson Synthesis"
DALLA CORT, Antonella;MANDOLINI, Luigi;
1980
Abstract
Product analysis, rate data, and effective molarity (e.m.) values have been obtained for the formation of catechol polymethylene ethers by the intramolecular alkylation of o-ω-bromoalkoxyphenoxides in Me 2SO-water (99 : 1, v/v). Twelve ring sizes were investigated in the range 6-32. Comparison with similar data for the reaction in EtOH-water (75 : 25, v/v) (except for n 32) showed that the e.m. values are largely independent of solvent despite the large solvent effect observed in both the cyclization reaction and the related intermolecular model reaction. Small effects only were observed in the medium ring region. The main possible factors playing a role in solvent effects on intramolecular cyclization have been critically analysed in the light of the data.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
