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


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Abstract

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.

About the authors

Ya. V. Veremeichik

Immanuel Kant Baltic Federal University

Author for correspondence.
Email: plem-kant@yandex.ru
Russian Federation, ul. Universitetskaya 2, Kaliningrad, 236040

D. N. Shurpik

Butlerov Institute of Chemistry

Email: plem-kant@yandex.ru
Russian Federation, Kremlevskaya ul. 18, Kazan, 420088

O. A. Lodochnikova

Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center

Email: plem-kant@yandex.ru
Russian Federation, ul. Arbuzova 8, Kazan, 420088

V. V. Plemenkov

Immanuel Kant Baltic Federal University

Email: plem-kant@yandex.ru
Russian Federation, ul. Universitetskaya 2, Kaliningrad, 236040

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