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Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides. 2020

Olga M Mulina, and Nataliya V Zhironkina, and Stanislav A Paveliev, and Dmitry V Demchuk, and Alexander O Terent'ev
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation.

Sulfonylated N-unsubstituted enamines were synthesized through a chain of chemical and electrochemical transformations via sulfonylation of vinyl azides. The disclosing of the N-unsubstituted enamines synthesis was based on a unique property of the azido group, which is its ability to eliminate the N2 molecule. Furthermore, a formal paradox is observed: a double bond reacts and a double bond is retained. Electrosynthesis proceeded in an undivided cell equipped with a graphite anode and a stainless steel cathode; NH4I was used as a supporting electrolyte.

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