2-benzopyrylium salts. xxxi : Analogs of reissert compounds from 2-benzopyrylium salts and sodium cyanide

2-benzopyrylium salts. xxxi : Analogs of reissert compounds from 2-benzopyrylium salts and sodium cyanide

Nucleophilic addition of a cyanide anion to 2-benzopyrylium salts I takes place at the first position and leads to stable isochromenes II, which are oxygen analogs of Reissert compounds. The structure II was confirmed by IR, 1H-NMR and 13C-NMR spectra. The latter spectra reveal clearly the cyano gro...

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Veröffentlicht in:Tetrahedron 1987, Vol.43 (2), p.409-414
Hauptverfasser: Balaban, Alexandru T., Gheorghiu, Mircea D., Shcherbakova, Irina V., Kuznetsov, Evgenii V., Yudilevich, Iosif A.
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Zusammenfassung:Nucleophilic addition of a cyanide anion to 2-benzopyrylium salts I takes place at the first position and leads to stable isochromenes II, which are oxygen analogs of Reissert compounds. The structure II was confirmed by IR, 1H-NMR and 13C-NMR spectra. The latter spectra reveal clearly the cyano group (which does not yield any observable stretching band) and give evidence for diastereotopic isopropyl carbons (unlike 1H-NMR spectra).
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)89971-3