On the Reaction of N-Formylbenzotriazole and Norbornene with NAlkylacetonitrilium Salts

Author(s): A. H. Moustafa .

Journal Name: Current Organic Chemistry

Volume 14 , Issue 17 , 2010

Become EABM
Become Reviewer

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.

Keywords: Nitrilium salts, N-formylbenzotriazole, norbornene, Ene product, iminium salts, octahydro-5, 8-methanonaphthridinium salts, salts, 8-methanonaphthridinium, Alkylacetonitrilium Salts, DDQ, Benzotriazole, amide group, IR spectra, oximes, 1H NMR spectra, ClCH2CH2Cl, Crystallization

Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 14
ISSUE: 17
Year: 2010
Page: [2012 - 2015]
Pages: 4
DOI: 10.2174/138527210792927500
Price: $58

Article Metrics

PDF: 4