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2-benzopyrylium salts. XXXVII. Oxygen analogs of reissert compounds : molecular structure and reactions with sodium hydroxide

✍ Scribed by Irina V. Shcherbakova; Evghenii V. Kuznetsov; Iosif A. Yudilevich; Olga E. Kompan; Alexandru T. Balaban; Aleksei H. Abolin; Alexander V. Polyakov; Yurii T. Struchkov

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 465 KB
Volume: 44
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)89812-4

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✦ Synopsis

The weak intensity of the CN stretching band in IR spectra for l-ayanoiso chromenes is obviousZy determined by the steric position of the CN group in the rroZecuZe, as it was estabUshed by X-ray structuraZ anclysis for the ayanide addition product (2d) of l-isopropyZ-3-methyZ-2-benzopyryZium sclts. Depending on the other substituent in position 1, 1-ayanoisochromenes in aqueous soLutions of sodium hydroxide eZiminate hydrogen ayanide (2a.b.e~ undergo inter-(2a.£J or intra:-rroZecuLar (2c.1j) reaydization. or hydroZysis of the ayano group in li; reaction products include a-naphthoZs ?c.!i:... f,-naphthoZ ?d, aaylchrysenes 5a,b. or the isochromene-amide J1i.; a stabZe l-aZkyUden7ilsochromene 3e wO:S-o'Etained. and the intermediaay of 3-hydroxy--1-aZkyZideneisochromenes was proved by their isoZation in the cases of 10c.4•

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2-benzopyrylium salts. xxxi : Analogs of

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✍ Alexandru T. Balaban; Mircea D. Gheorghiu; Irina V. Shcherbakova; Evgenii V. Kuz 📂 Article 📅 1987 🏛 Elsevier Science 🌐 French ⚖ 420 KB

Nucleophilic aldition of u cyanide anion to 2-benwpyryliwn salt8 I takes place at the firet position end led8 to stable i8ochzvmene8 II, which are oxygen anabgs of Reissert aqXUnd8. The structure II uaa a~nfirmed by IR, 'H-NM? and '3C-NMR spectra. The tatter epectra reveal clearly the cyarr, gzup (w

A.T. Balaban, M.D. Gheorghiu, I.C. Shche

A.T. Balaban, M.D. Gheorghiu, I.C. Shcherbakova, E.V. Kuznetsov and I.A. Yudilevich, 2-benzopyrylium salts—XXXI. Analogs of reissert compounds from 2-benzopyrylium salts and sodium cyanide: Tetrahedron 43, 409 (1987)

📂 Article 📅 1987 🏛 Elsevier Science 🌐 French ⚖ 27 KB

The footnote is marked with an asterisk after the only text's mention of the reference 1141: . . . and the only example of 1 -cyano-1 -IV-R-amidoisochromenes [ 141. + \*Nevertheless the sharp CN stretching band at 2230 cm-' can be discovered in cyanoisochromenes II a-h after an accumulation and a sc