On January 15, 2007, Roy, Chandra D.; Brown, Herbert C. published an article.Electric Literature of 2160-93-2 The title of the article was Stability of boronic esters – Structural effects on the relative rates of transesterification of 2-(phenyl)-1,3,2-dioxaborolane. And the article contained the following:
Relative rates of reaction of the achiral cyclic phenylboronic ester 2-(phenyl)-1,3,2-dioxaborolane with a wide variety of structurally modified diols, have been studied to understand the factors influencing the relative stabilities of boronic esters. It is found that the alkyl substituents on the α-carbons of diols slow down the transesterification, but produce thermodynamically more stable boronic ester. Six-membered boronic esters are thermodynamically more stable than their corresponding five-membered analogs. Amongst cyclic 1,2-diols, cis-1,2-cyclopentanediol displaces ethylene glycol instantaneously whereas trans-1,2-cyclopentanediol is totally unreactive, which suggests that the cis-stereochem. of the 1,2-diol is a prerequisite for transesterification. Among the 1,5-diols, diethanolamine displaces ethylene glycol quite rapidly forming a more stable bicyclic chelate in which nitrogen is attached to boron by a coordinating bond (as evident by 11B NMR spectroscopy). The oxygen atom of di(ethylene glycol) and the sulfur atom of 2,2′-thiodiethanol do not assist in displacing the ethylene glycol from their boronic esters. The experimental process involved the reaction of 2,2′-(tert-Butylazanediyl)diethanol(cas: 2160-93-2).Electric Literature of 2160-93-2
The Article related to phenyl dioxaborolane preparation transesterification kinetics diol, cyclic phenylboronic ester preparation transesterification kinetics diol substituent effect, Organometallic and Organometalloidal Compounds: Boron Compounds and other aspects.Electric Literature of 2160-93-2
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