Synthesis of cyclic sulfonamides by reaction of  N -sulfinyl-3-(trifluoromethyl)aniline with norbornenes

Ya. V. Veremeichik; D. N. Shurpik; O. A. Lodochnikova; V. V. Plemenkov

doi:10.1134/S1070428016010176

Synthesis of cyclic sulfonamides by reaction of N-sulfinyl-3-(trifluoromethyl)aniline with norbornenes

Autores: Veremeichik Y.V.¹, Shurpik D.N.², Lodochnikova O.A.³, Plemenkov V.V.¹
Afiliações:
1. Immanuel Kant Baltic Federal University
2. Butlerov Institute of Chemistry
3. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center
Edição: Volume 52, Nº 1 (2016)
Páginas: 92-95
Seção: Article
URL: https://bakhtiniada.ru/1070-4280/article/view/213542
DOI: https://doi.org/10.1134/S1070428016010176
ID: 213542

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N-Sulfinyl-3-(trifluoromethyl)aniline reacted with bicyclo[2.2.1]hept-2-ene and bicyclo[2.2.1]-hepta-2,5-diene to give the corresponding Diels‒Alder adducts which were oxidized to 8-trifluoromethyl-2,3,4,4a,6,10b-hexahydro-5λ⁶-1,4-methanodibenzo[c,e][1,2]thiazine-5,5(1H)-diones. The cycloaddition occurred predominantly with participation of the S=N–C¹=C⁶ fragment of N-sulfinyl-3-(trifluoromethyl)aniline and exclusively at the endo side of bicyclo[2.2.1]heptenes.