The product imidoyl chloride can be hydrolyzed to give the amide, trapped with other nucleophiles, or undergo halide abstraction with silver salts to form an acyl nitrilium intermediate.[3]
The reaction is of some theoretical interest, as kinetic measurements[4] and DFT studies[5] have indicated that the addition occurs in one step, without the intermediacy of a tetrahedral intermediate that is commonly proposed for carbonyl addition reactions.
^Tron, Gian; El Kaïm, Laurent; La Spisa, Fabio (2014-03-05). "The Nef Reaction of Isocyanides". Synthesis. 46 (7): 829–841. doi:10.1055/s-0033-1338596. ISSN0039-7881.
^Westling, Mark; Smith, Richard; Livinghouse, Tom (April 1986). "A convergent approach to heterocycle synthesis via silver ion mediated .alpha.-ketoimidoyl halide-arene cyclizations. An application to the synthesis of the erythrinane skeleton". The Journal of Organic Chemistry. 51 (8): 1159–1165. doi:10.1021/jo00358a001. ISSN0022-3263.
^Ugi, Ivar; Fetzer, Uwe (April 1961). "Isonitrile, III. Die Addition von Carbonsäurechloriden an Isonitrile". Chemische Berichte (in German). 94 (4): 1116–1121. doi:10.1002/cber.19610940433. ISSN0009-2940.
^Chéron, Nicolas; El Kaïm, Laurent; Grimaud, Laurence; Fleurat-Lessard, Paul (2011-09-08). "A Density Functional Theory Study of the Nef-Isocyanide Reaction: Mechanism, Influence of Parameters and Scope". The Journal of Physical Chemistry A. 115 (35): 10106–10112. Bibcode:2011JPCA..11510106C. doi:10.1021/jp205909d. ISSN1089-5639. PMID21786773.
