Conclusions
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1.
The protonation of asymmetrical acetals on chemical ionization (CI) in methane takes place preferentially through a more basic oxygen atom.
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2.
In a protonated molecular ion obtained on CI in isobutane asymmetrical acetals preferentially eliminate the alkoxy group having a less basic oxygen atom.
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3.
The rate of elimination of the alcohol from the protonated molecular ion of an acetal is determined by the substituent in the carbonyl part of the molecule to an appreciably greater extent than in the alcohol part.
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4.
The CI spectra of most acetals (reagent gases methane or isobutane) provide information on the molecular weight of the compounds and also on the substituents in the carbonyl and alcohol parts of the molecule.
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Literature cited
L. A. Yanovskaya, S. S. Yufit, and V. F. Kucherov, The Chemistry of Acetals [in Russian], Nauka, Moscow (1975).
M. S. Munson and F. H. Field, J. Am. Chem. Soc.,89, 1047 (1967).
H. B. Mark and G. A. Richnitz, Kinetics in Analytical Chemistry, Wiley (1968).
C. A. Bunton, T. A. Lewis, D. R. Llewellyn, and C. A. Vernon, J. Chem. Soc, 4419 (1955).
P. Longeviale, G. W. Milne, and H. M. Fales, J. Am. Chem. Soc.,96, 6666 (1973).
J. Dzidik and T. A. McCloskey, J. Am. Chem. Soc.,93, 4955 (1971).
P. Broon and C. J. Djerassi, J. Am. Chem. Soc.,87, 4559 (1965).
A. A. Solov'ev, V. I. Kadentsev, O. S. Chizhov, D. N. Bel'kind, and A. G. Savel'ev, Prib. Tekh. Eksp., No. 2, 223 (1976).
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Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 7, pp. 1518–1525, July, 1981.
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Borisova, I.A., Kadentsev, V.I., Zlotskii, S.S. et al. Behavior of acetals under chemical ionization conditions. Russ Chem Bull 30, 1219–1224 (1981). https://doi.org/10.1007/BF01417976
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DOI: https://doi.org/10.1007/BF01417976