Phenyl chloroformate nitrile synthesis

An alternative common method of nitrile oxide synthesis, frequently referred to as the Mukaiyama method (60JA5339), involves dehydration of primary nitroalkanes using, for example, phenyl isocyanate in the presence of a catalytic amount of triethylamine (Scheme 5). Phosphorus oxychloride (730S59 90S817), chloroformate esters (86BCJ2827), aryl... 

Butylation of phenylacetonitrile with aqueous NaOH, as shown in Scheme 25, proceeds faster by use of high DF (>0.5) anion exchange resins.The strongly alkaline conditions degrade the quaternary ammonium ions of the catalyst. Catalyst (64) (1% DVB) is active for alkylation of phenylacetonitrile and benzyl phenyl ketone, and for Williamson ether synthesis, and it is much more stable in base than AERs. AERs in OH form are catalysts for dichlorocyclopropane syntheses from alkenes, chloroform and solid sodium hydroxide, and for dehydration of amides to nitriles. AERs in the appropriate hydroxide, acetate, or cyanide form are catalysts for aldol condensations, Michael reactions, Knoevenagel condensations, cyanoethylations and cyanohydrin syntheses. " ... 

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