Chemical Communications

Investigation of the factors controlling the regioselectivity of the hydroboration of fluoroolefins

PV Ramachandran, MP Jennings

Index: Ramachandran, P. Veeraraghavan; Jennings, Michael P. Chemical Communications, 2002 , # 4 p. 386 - 387

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Citation Number: 20

Abstract

On the basis of the above rate expressions, we envisaged that (Sia 2 BH) 2 might reveal different reactivity toward perfluoroalkylethylenes. Indeed, the reaction of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro -1-octene (1a) with (Sia 2 BH) 2 proceeded to completion within 14 h at rt, as revealed by 11 B NMR spectroscopy. Alkaline H 2 O 2 oxidation provided a 3∶2 regioisomeric mixture favoring the anti-Markovnikov alcohol. In all probability, the lack of regioselectivity might be due to ...