3-Methyl-benzonitrile

The hydrogenation of benzonitrile catalyzed by 21 afforded under 75 bar of H2 and at 140°C in THF a 90% conversion revealing a TOF of 180 h forming 66% dibenzylamine, 24% tribenzylamine, and 10% dibenzylimine within 1 h. The presence of EtsSiH as a co-catalyst improves the catalytic performance with respect to both activity and selectivity. When 25 equiv. of EtsSiH with respect to the rhenium catalyst was applied, the same reaction showed a conversion of 99% with a TOF of 396 h within 0.5 h forming 90% dibenzylamine, 4% tribenzylamine, and 6% dibenzylimine. The generality of the reaction was probed by applying the Re(I) catalysts 22-24 under the same conditions in the hydrogenation of 3-methyl-benzonitrile, thiophen-2-carbonitrile, cyclohexanenitrile, and benzyl nitrile (Scheme 27). 

Nitio-a,ozy.3-methyl-benzonitril 10 1100, 2 (Oder 6)-mtio-3-ozy-4-methyl-benzoiiitril 10. 238. 

Also obtained by reaction of ethylmagnesium bromide with 2-methoxy-3-methyl-benzonitrile (69%) [6973]. 

Substituted benzyl fluorides react with sodium bcnzenethiolate yielding substituted (ben-zylsulfanyl)benzenes.1 The reactions were studied kinetically and found to be of the SN2 type.1 As expected, from the chloro-, cyano-, methoxy-, and methylbenzyl fluorides tested, 4-(fluoro-methyl)benzonitrile is the most reactive derivative. 

A comprehensive study of the solvent dependence of the photophysical properties of 9,9 -bianthryl shows that the fluorescence lifetime is essentially constant in low polarity solvents. In more polar solvents, light-induced electron transfer occurs to form a perpendicular ICT state having D2d symmetry and which is weakly fluorescent. Reports have appeared that describe the photoisomerization of 4-nitrobenzaldehyde, 5-hydroxytropolone, 4-hydroxybenzonitrile, methyl-benzonitrile, and cinnamaldehyde. ... 

CuHgBrgNOg 3.5-Dibrom-4-acetojy.2.6-di= methyl-benzonitril 10 II162. 

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