Science of Synthesis

Kubik, S., Science of Synthesis, (2010) 41, 529.

Generation of alkenediazonium compounds from the tosylhydrazones of 2-haloaldehydes with Lewis acids proceeds in two steps via 1-(tosylazo)alk-1-ene derivatives (see Section ‌41.7.2.1.3.1‌). If this reaction is performed with bases such as triethylamine, it stops after HX elimination, allowing the isolation of 1-(tosylazo)alk-1-enes.[‌123‌,‌135‌] 4-Toluenesulfinate elimination can then be induced in a separate step by treating these compounds with Lewis acids such as tin(IV) chloride or antimony(V) chloride. ‌Table 5‌ lists examples of alkenediazonium compounds that have been prepared using this method.

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