Regiocontrolled Opening of 2-Methyltetrahydrofuran with Various Boron Reagents*
Chandra D. Roy A BA 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.
Australian Journal of Chemistry 59(9) 657-659 https://doi.org/10.1071/CH06272
Submitted: 30 July 2006 Accepted: 20 August 2006 Published: 19 October 2006
Abstract
Regiocontrolled halogenative cleavage of 2-methyltetrahydrofuran with various B-bromoboranes, by a predominantly SN2-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.
Acknowledgment
Financial support from the Purdue Borane Research Fund is greatly appreciated.
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* 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).
