Boron trifluoride 2-octanol reduction

The formation of alkenes and alkene-related polymerization products can seriously reduce the yields of desired alkane products from secondary alcohols, which can undergo elimination reactions. For example, reduction of 2-octanol at 0° with boron trifluoride gas in dichloromethane containing 1.2 equivalents of tri-ethylsilane gives only a 58% yield of n-octane after 75 minutes (Eq. II).129 The remainder of the hydrocarbon mass comprises nonvolatile polymeric material.126... 

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