The reaction enthalpy and rate of reduction of 1,1-diphenylethylene (DPE) by the Lewis pair of tris-pentafluorophenylborane (BCF) and diethyl ether in dichloromethane have been determined by mixing calorimetry.  At 50 �C and 200 psi hydrogen, in the presence of one equivalent of BCF and 4.5 equivalents of diethyl ether, DPE is reduced to the corresponding alkane in ca. 90 minutes in an exothermic reaction. The products determined by NMR spectroscopy showed >99% conversion to the reduced product 1,1-diphenylethane. The rate of conversion as monitored by the time dependent heat flow shows first order kinetics over several half-lives providing a rate of conversion of the olefin to the alkane of 2.1�.2 x10-3 s-1 at 200 psi hydrogen while integration of the total heat provides a measure of the reduction reaction enthalpy of ca. -119 � 5 kJ/mol.

Kinetic and thermodynamic study of the catalytic reduction of olefins by frustrated Lewis pairs

248th National Meeting (2014)

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