Opening of the epoxide bridge in 3a,6-epoxyisoindol-1-ones by the action of B[F.sub.3] x [Et.sub.2]O in acetic anhydride

The opening of the epoxide bridge in N-substituted 2,3,7,7a-tetrahydro-3a,6- epoxyisoindol-1-ones by the action of B[F.sub.3] x [Et.sub.2]O in acetic anhydride at 25°C over 1 h proceeds through an [S.sub.N]1 mechanism. The allylic type cation formed in the first step is stabilized by the addition of...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2012-06, Vol.48 (3), p.514
Main Authors: Zubkov, F.I, Zaytsev, V.P, Puzikova, E.S, Nikitina, E.V, Khrustalev, V.N, Novikov, R.A, Varlamov, A.V
Format: Article
Language:English
Subjects:
Chemical properties
Diels-Alder reaction
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Summary:The opening of the epoxide bridge in N-substituted 2,3,7,7a-tetrahydro-3a,6- epoxyisoindol-1-ones by the action of B[F.sub.3] x [Et.sub.2]O in acetic anhydride at 25°C over 1 h proceeds through an [S.sub.N]1 mechanism. The allylic type cation formed in the first step is stabilized by the addition of an acetoxy group at C-5 in the isoindole system to give a mixture of cis and trans isomers of 5,6-diacetoxy- 2,3,5,6,7,7a-hexahydroisoindol-1-ones, which are aromatized under these conditions over 24 h to give 2,3-dihydro1H- isoindol-1-ones. Keywords: 3a,6-epoxyisoindole, furan, furfurylamine, isoindole, 7- oxabicyclo[2.2.1]heptene, aromatization, intramolecular Diels-Alder reaction.
ISSN:0009-3122
1573-8353