Regiocontrolled Opening of 2-Methyltetrahydrofuran with Various Boron Reagents

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Contents Vol 59(9)

doi:10.1071/CH06272

Regiocontrolled Opening of 2-Methyltetrahydrofuran with Various Boron Reagents*

Chandra D. Roy

^A Department of Chemistry, Herbert C. Brown Center for Borane Research, Purdue University, West Lafayette, IN 47907, USA. Email: chandra0919@gmail.com
^B Present address: EMD Biosciences, Inc., San Diego, CA, USA.





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Australian Journal of Chemistry 59(9) 657–659 http://dx.doi.org/10.1071/CH06272
Submitted: 30 July 2006 Accepted: 20 August 2006 Published online: 19 October 2006

Abstract

Regiocontrolled halogenative cleavage of 2-methyltetrahydrofuran with various B-bromoboranes, by a predominantly S_N2-type mechanism favouring the formation of primary bromide, is described. A comparative study of the relative reactivities of BH₂Br·SMe₂, BHBr₂·SMe₂, BBr₃, (MeO)₂BBr, and MeOBBr₂ revealed that the newly synthesized (MeO)₂BBr is a highly promising regioselective reagent, especially at lower temperatures.

^* This paper is dedicated to the memory of my mentor, the late Professor Herbert C. Brown (1912–2004). The work described herein was carried out at Purdue University during my stay as a post-doctoral research associate (1995–2001).