Abstract
On the basis of the data from the 1H, 13C, and 15N NMR spectra it was established that perhydro-1,3,2-dioxazine has the chair conformation with the equatorial orientation of the NH proton; the barrier to inversion at the N atom is δG≠=21.9 kcal/mole. The preferred conformer of its 4-methyl derivative has the 2e,4e configuration. Stereospecific spin-spin coupling constants 4Je-HCONH-e, 3J13CONH-e, and 3J15NOCH-e were obtained for these compounds. 1,3,2-Dioxazolidine has a “bent envelope” conformation with the axial orientation of the NH proton; a stereospecific spin-spin coupling constant 4Je-HCONH-e was obtained, and the invariability of the PMR spectrum at 170‡C was demonstrated.
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Communication 58 of the Series “Asymmetric Nitrogen,” for Communication 57 see [1]; Communication 35 of the Series “Geminal Systems,” for Communication 34, see [2].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 24, No. 3, pp. 396–402, March, 1988.
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Chervin, I.I., Nosova, V.S., Rudchenko, V.F. et al. Stereochemistry and configurational stability of cyclic NH- and N-dimethylcarbamoyldialkoxyamines. Chem Heterocycl Compd 24, 325–332 (1988). https://doi.org/10.1007/BF00475334
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DOI: https://doi.org/10.1007/BF00475334