Organic Letters, volume 22, issue 5, pages 1818-1824
Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides
O M Mulina
1
,
Nataliya V Zhironkina
1, 2
,
Publication type: Journal Article
Publication date: 2020-02-20
Journal:
Organic Letters
scimago Q1
wos Q1
SJR: 1.245
CiteScore: 9.3
Impact factor: 4.9
ISSN: 15237060, 15237052
PubMed ID:
32077294
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
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.
Found
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