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LETTERS

TO THE EDITOR

BASIC DEUTERIUM EXCHANGE IN THE INDOLIZINE SERIES S. I. Bobrovskii, E. V. Babaev, and Yu. G. Bundel' UDC 547.759'828.110.2

Using 2-methyl-6-nitroindolizine as a strated selective basic deuterium exchange for 5 h in a solution of 4 mole/liter MeONa tensity for the lowest field signal for 5-H the spectrum remained unchanged.

model indolizine we have for the first time demonat position 5o Thus a sample of I was refluxed in MeOD. In its NMR spectrum the integrated infell more than 30 times while the remainder of

NO 2

.

Me

NO2/~. D II

v

,~e

D I

Monodeuteration was confirmed by mass spectrometric data. Solution of i in CY~COOH led to formation of the 3H-indolizinium cation (II) which had "shifted" PMR signals and allowed a specific assignment of the deuterium exchange position (the spectra of non-deuterated I and II are given in [I]). Under the same conditions it was found that 2-methyl-8-nitroindolizine did not undergo deuterium exchange. LITERATURE CITED I. S.I. Bobrovskii, E. V. Babaev, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 2, 203 (1987).

M. V. Lomonosov State University, Moscow, 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1285, September, 1987. Original article submitted February 2, 1987.

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0009-3122/87/2309-1032512.50

9 1988 Plenum Publishing Corporation