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On the Reaction of N-Formylbenzotriazole and Norbornene with N-Alkylacetonitrilium Salts
Faculty
Science
Year:
2010
Type of Publication:
Article
Pages:
2012-2015
Authors:
Moustafa, A. H
Journal:
CURRENT ORGANIC CHEMISTRY BENTHAM SCIENCE PUBL LTD
Volume:
14
Research Area:
Chemistry
ISSN
ISI:000284827000011
Keywords :
Nitrilium salts, N-formylbenzotriazole, norbornene, Ene product, iminium salts, octahydro-5, 8-methanonaphthridinium salts
Abstract:
Reaction of N-methyl/isopropylacetonitrilium hexachloroantimonate 1a, b with N-formylbenzotriazole 2 afforded the corresponding iminium salts 4a, b; of which 4a reacts with the oxime derivatives 5a-d to give the corresponding N-oxyiminium salts 6a-d in a good yield (60-92 \%). Reaction of N-methylacetonitrilium hexachloroantimonate 1a with norbornene (7) furnished the new ring system 1,4,4a, 5,6,7,8,8a-octahydro-5,8-methano-4(2-norbornyl)-naphthridinium hexachloroantimonate 10 in 85 \% yield. The Treatment of 10 with DDQ oxidized the two bridged protons and afforded 1,4,5,6,7,8-hexahydro-5,8-methano-4(2-norbornyl)-naphthrdinium hexachloroantimonate 11 in 80\% yield.
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