Chlorination of Conjugated Nitroalkenes with PhICl2 and SO2Cl2 for the Synthesis of α-Chloronitroalkenes

Chlorination of Conjugated Nitroalkenes with PhICl2 and SO2Cl2 for the Synthesis of α-Chloronitroalkenes Full article

Journal

Synthesis-Stuttgart
ISSN: 1437-210X , E-ISSN: 0039-7881

Output data

Year: 2020, Volume: 52, Number: 18, Pages: 2679-2688 Pages count : 10 DOI: 10.1055/s-0040-1707396

Authors

Fadeeva Anastasia A. ¹ , Ioffe Sema L. ^2,1 , Tabolin Andrey A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
2	Higher Chemical College, D. Mendeleev University of Chemical Technology of Russia

Chlorination of conjugated nitroalkenes with iodobenzene dichloride or sulfuryl chloride to give target α-chloronitroalkenes in good yields is described. Details of the procedure depend on the donating ability of the nitroalkene substituents. The activity of the described chlorinating agents increases in order ‘PhICl2/Py’ < ‘SO2Cl2’ < ‘SO2Cl2/HCl’ with the former producing the best yields for highly donating substrates and the latter for non-activated groups. An autocatalytic role of hydrogen chloride and the chemoselectivity of chlorination were also demonstrated.

Fadeeva A.A. , Ioffe S.L. , Tabolin A.A.
Chlorination of Conjugated Nitroalkenes with PhICl2 and SO2Cl2 for the Synthesis of α-Chloronitroalkenes
Synthesis-Stuttgart. 2020. V.52. N18. P.2679-2688. DOI: 10.1055/s-0040-1707396 WOS Scopus OpenAlex

≡ Web of science:	WOS:000563008300009
≡ Scopus:	2-s2.0-85093865303
≡ OpenAlex:	W3024093699