Conclusions
Quantum-chemical calculations show the substituted carbon atom to be the preferred center for nucleophilic attack on 2-methyl- and 2-aminomethylethyleneimines (2-MEI and 2-AMEI), ethyleneimine ring opening resulting from rupture of the weakened C-N bonds at these atoms.
Separation of the dimer fractions from polymerized 2-MEI and 2-AMEI followed by chromatographic and chromato-mass spectral analyses showed the structures and relative amounts of the various dimers to be consistent with the results of the calculations.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1498–1503, July, 1977.
The authors wish to thank V. Ya. Bespalov who furnished the computer program, and V. G. Zaikin who recorded and interpreted the mass spectra.
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Avakyan, V.G., Gromova, G.L., Timofeeva, L.M. et al. Electron structures of C-substituted ethyleneimines and certain aspects of the mechanism of nucleophilic opening of three-membered rings 1. Dimerization of C-substituted ethyleneimines. Russ Chem Bull 26, 1376–1380 (1977). https://doi.org/10.1007/BF00928508
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DOI: https://doi.org/10.1007/BF00928508