Abstract
The mass spectra of substituted 3,9-diazabicyclo- and 3,9-oxaazabicyclo[3.3.1]-nonanes were studied as a function of competitive distribution of the charge between the N3 and N9 and O3 and N9 atoms and the properties of the substituents attached to the heteroatoms. It is shown that a characteristic peculiarity of the fragmentation of 3,9-diazabicyclo[3.3.1]nonanes is fragmentation of the molecular ion with an open structure that is formed by cleavage of the C1-C2 bond. The formation of an amine fragment with retention of the bicyclic structure with an exocyclic double bond attached to the quaternary N9 atom is characteristic for 3,9-oxaazabicyclo[3.3.1]nonanes. It is shown that this sort of behavior of the investigated compounds is determined by their structures and the properties of the heteroatoms in the saturated bicyclic systems.
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Communication 12 from the series “Application of mass spectrometry in structural and stereochemical studies.” See [1] for Communication 11.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 229–235, February, 1981.
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Ermakov, A.I., Sheinker, Y.N. Mass-spectrometric study of 3,9-diazabicyclo- and 3,9-oxaazabicylo[3.3.1]nonanes. Chem Heterocycl Compd 17, 166–171 (1981). https://doi.org/10.1007/BF00507250
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DOI: https://doi.org/10.1007/BF00507250