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New Evidence for the Mechanism of the tin(II) Chloride Catalyzed Reactions of Vicinal Diols With Diazodiphenylmethane in 1,2-dimethoxyethane

New Evidence for the Mechanism of the tin(II) Chloride Catalyzed Reactions of Vicinal Diols With Diazodiphenylmethane in 1,2-dimethoxyethane

S Pétursson

Carbohydr Res. 2001 Apr 12;331(3):239-45.

PMID: 11383893

Abstract:

A kinetic study of the tin(II) chloride catalyzed reaction of diazodiphenylmethane with ethylene glycol in dimethoxyethane is reported. The preparation and characterization of ethylene glycol monodiphenylmethyl ether, the main product from this reaction, is also reported as well as the preparation of the two diphenylmethyl monoethers of methyl 4,6-O-benzylidene-alpha-D-glucopyranoside. An unexpected relationship between the concentration of ethylene glycol and the pseudo first-order rate constant, k', was observed in these reactions. For low concentrations of ethylene glycol (below 0.06 M), k' increases with increasing concentration of the diol. This trend is reversed for high concentrations of ethylene glycol (from about 0.06 to about 0.2 M). The apparent rate constant was also inversely related to the initial concentration of diazodiphenylmethane for the concentrations investigated. These results make the previously proposed involvement of a 1,3,2-dioxastannolane intermediate very unlikely [Petursson, S.; Webber, J.M. Carbohydr. Res. 1982, 103, 41-52]. The results suggest that more likely intermediates for these reactions involve tin(II) chloride complexes in a dynamic equilibrium with the diol.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP3590598	2,2-Dibutyl-[1,3,2]dioxastannolane		3590-59-8	Price

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