Oxidative addition of N-aminophthalimide to 3,4-dihydro-2H-thiopyrans, their S-oxides, and S,S-dioxides
2022
Merkulova, Ekaterina A. | Kolobov, Aleksey V. | Kuznetsov, Mikhail A. | Spiridonova, Dar'ya V. | Pankova, Alena S.
Selectivity of nitrene addition to the CCS fragment depends on the oxidative state of the sulfur atom as has been exemplified on various derivatives of 3,4-dihydro-2H-thiopyran under conditions of oxidative aminoaziridination. A unique structure with 2-thia-7-azabicyclo[4.1.0]heptane-2,2-dioxide core was obtained via addition of nitrene to the CC bond of thiopyran S,S-dioxide. For an unoxidized thiopyran, only en(phthaloyl)hydrazine resulted after cleavage of the initially formed aziridine. S-Oxide trapped the nitrene by the sulfur atom to form the sulfoximine leaving the double bond unaffected.
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