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Contents Vol 64(11)

Preparation and Properties of (Hydroxymethyl)boronic Acid and its Pinanediol Ester

Donald S. Matteson A
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, Washington State University, Pullman, WA 99164-4630 USA. Email: dmatteson@wsu.edu

Australian Journal of Chemistry 64(11) 1425-1429 https://doi.org/10.1071/CH11289
Submitted: 14 July 2011  Accepted: 5 August 2011   Published: 16 November 2011

Abstract

Hydrolysis of diisopropyl (bromomethyl)boronate followed by reaction with pinanediol provides an efficient route to pinanediol (hydroxymethyl)boronate (12), a useful intermediate for asymmetric synthesis. The stability of (hydroxymethyl)boronic acid (10) and its ester 12 have been examined by NMR spectroscopy. Heating for 1 h in acidic D2O does not degrade 10 and only affects the pinanediol moiety of 12. Base does not degrade 10 or 12 in several days at 20–25°C, but converts either to DCH2OD and CH3OD in a few h at 90–98°C, with a large H/D isotope effect. Pinanediol (bromomethyl)boronate with sodium hydroxide in D2O yields a gross mixture of products.


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