Email this article 7-Azabicyclo[2.2.1]heptadienes in electrophilic chalcogenation reactions
- Authors: Gavrilova A.Y.1, Nechaev M.A.1, Aparshov D.A.1, Arkhipenko S.Y.1, Antipin R.L.1, Bondarenko O.B.1, Zyk N.V.1,2
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Affiliations:
- Department of Chemistry, M. V. Lomonosov Moscow State University
- Institute of Physiologically Active Compounds, Russian Academy of Sciences
- Issue: Vol 66, No 3 (2017)
- Pages: 511-522
- Section: Full Articles
- URL: https://ogarev-online.ru/1066-5285/article/view/240242
- DOI: https://doi.org/10.1007/s11172-017-1765-0
- ID: 240242
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Abstract
Reactions of electrophilic chalcogenation (sulfenylation and selenenylation) of 7-azabicyclo[2.2.1]heptadiene derivatives with electron-withdrawing substituents at the nitrogen atom and the double bond were found to proceed trans-stereospecifically with the formation of 1,2-addition products, resulting from the exo-attack by the electrophile. In the case of 2-tosyl-7-azanorbornadiene, the reaction is regiospecific: the electrophilic species exclusively adds to the carbon atom at position 6. A comparative analysis of the behavior of dimethyl bicyclo-[2.2.1]heptadiene-2,3-dicarboxylate and its 7-aza analogs in the AdE reactions was carried out.
About the authors
A. Yu. Gavrilova
Department of Chemistry, M. V. Lomonosov Moscow State University
Author for correspondence.
Email: augava@gmail.com
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
M. A. Nechaev
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: augava@gmail.com
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
D. A. Aparshov
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: augava@gmail.com
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
S. Yu. Arkhipenko
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: augava@gmail.com
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
R. L. Antipin
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: augava@gmail.com
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
O. B. Bondarenko
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: augava@gmail.com
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
N. V. Zyk
Department of Chemistry, M. V. Lomonosov Moscow State University; Institute of Physiologically Active Compounds, Russian Academy of Sciences
Email: augava@gmail.com
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991; 1 Severnyi proezd, Chernogolovka, Moscow Region, 142432
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