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

✍ Scribed by Alexandru T. Balaban; Mircea D. Gheorghiu; Irina V. Shcherbakova; Evgenii V. Kuznetsov; Iosif A. Yudilevich

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
420 KB
Volume
43
Category
Article
ISSN
0040-4020

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✦ Synopsis

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 (which does rwt yield any observable stretching bond) end give evidence for diastereotopic iwpzvpyl carbons (unlike 'H-NM? spectra).

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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

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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.