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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Regiocontrolled Opening of 2-Methyltetrahydrofuran with Various Boron Reagents*

Chandra D. Roy A B
+ Author Affiliations
- Author Affiliations

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.

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.


References


[1]   (a) D. P. Curran, D. Scholz, Monatsh. Chem. 1977, 108,  1401.
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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).