Isoselenocyanates isonitriles

The Bu3SnH decyanation of isonitriles (Scheme 16) was first reported by Saegusa, and was developed as a general, mild method for reductive deamination by Barton and coworkers who initially showed that a variety of isonitriles, isothiocyanates and isoselenocyanates reacted with Bu3SnH under the usual free radical conditions (reflux in benzene, toluene or xylene with catalytic AIBN) to give good yields of the corresponding hydrocarbon. In concert with the normal order of radical stability, primary... 

A review on the acid promoted decomposition of a-diazoketones contains some steroidal examples.88 The full account was reported of the conversion of a-azido-ketones into cyano-carboxylic acids promoted by bromine in acetic acid.89 A general review on new reagents in natural product chemistry included the deamination of amines via the isonitriles, isothiocyanates, and isoselenocyanates reported... 

The 2-imino-l,3-oxaselenane ring system 55 can be prepared by the reaction of the sterically hindered isonitrile 54 with an acetylenic alcohol in the presence of selenium, cuprous iodide, and a base (Equation 11) <2004JOC4845>. This reaction probably occurs via the formation of an intermediate isoselenocyanate. The product was not formed in the absence of Cul. 

Without additional reagents Isoselenocyanates from isonitriles... 

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