- Regiocontrolled opening of 2-methyltetrahydrofuran with various boron reagents
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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, BHBr 2?SMe2, BBr3, (MeO)2BBr, and MeOBBr2 revealed that the newly synthesized (MeO)2BBr is a highly promising regioselective reagent, especially at lower temperatures. CSIRO 2006.
- Roy, Chandra D.
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- Dimethoxyboron bromide - A new, efficient, regio- and chemoselective reagent for the conversion of terminal epoxides into bromohydrins
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Dimethoxyboron bromide, (MeO)2BBr, easily prepared in excellent yield from boron tribromide and trimethyl borate, is a new, efficient, regio- and chemoselective reagent useful for the halogenative cleavage of compounds containing epoxy groups into vicinal bromohydrins in the presence of ether, acetal, ketal, N-oxide, and sulfoxide groups, at low temperatures (-78°C).
- Roy, Chandra D.,Brown, Herbert C.
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p. 639 - 641
(2007/10/03)
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