Nitrosyl cyanide Diels-Alder reactions

Nitrosyl cyanide (109) has been briefly examined as a dienophile by Kirby et This intermediate can be generated from nitrosyl chloride and silver cyanide (equation 42) and trapped with 9,10-diinethyl-anthracene to yield adduct (110). As with acyl nitroso compounds, this adduct can be used as a stable source of (109) via a retro Diels-Alder reaction. 

Several examples of hetero Diels-Alder reactions with nitrosyl cyanide are presented in Scheme 3-XV. Orientation of addition to unsymmetrical dienes generally corresponds to that of aryl- and chloroalkylnitroso compounds (vide supra). 

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