Science of Synthesis

Wu, Y.-Q., Science of Synthesis, (2005) 18, 33.

There are only a few examples relating to the reactivity and synthetic utility of sulfinyl cyanides. On the other hand, tosyl cyanide,[‌41‌] a typical sulfonyl cyanide, has been extensively studied, and found to be useful for the preparation of a variety of aromatic and aliphatic heterocycles, for the stereospecific synthesis of alk-2-enenitriles, and for the α-cyanation of ketone enolates. The reaction of nucleophiles with tosyl cyanide is different from their reaction with acyl cyanides (R1COCN), in which the carbonyl group is attacked instead. Apparently, the activating influence of the neighboring sulfonyl group enhances the reactivity of the cyano group considerably so that it resembles the reactivity of the cyano group in cyanates, thiocyanates, and cyanogen halides. The reaction of tosyl cyanide with triphenylphosphine, however, takes a different course: no transfer of the cyano group is observed; instead the sulfonyl group is reduced to give 4-tolyl thiocyanate.

References

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• 8.Meeeee-Meee, (8888) M 8, 888.