13C NMR spectra of stereoisomeric derivatives of bicyclo[2.2.1]-hept-5-ene and 3-oxatricyclo[3.2.1.02,4]octane

Azabrendanes. II. Chemo-, regio- and stereoselective transformation of 3-oxatricyclo[3.2.1.02,4]octane-endo-6-carbonitrile in reaction with lithium aluminum hydride

“…[12]. 13 C NMR spectra of the epoxides contain the signals of the epoxy ring carbon nuclei in the region d ‫ס‬ 49 to 51 which is in agreement with the literature [13]. Table 1 lists the parameters of carbon spectra and those of 14 N and 17 O NMR spectra for epoxides 3a, 3b, and 4b.…”

“…In contrast to epoxide (4a), hydroxyamine (5) has an H 9n proton multiplet in the strong field (d ‫ס‬ 0.86) undergoing splitting with respect to the H 9x proton, the constant being 12.9 Hz, as well as for the protons H 6 and H 8s with the equal constants 2.1 Hz. Table 3 lists the results of the 13 C NMR spectrum of the tricyclic amine (5). The signals were assigned by comparison with the spectrum for the ether (7) for which an experiment on 13 C(H) selective double resonance had been made.…”

“…Reaction of amine (5) with p-nitrophenyloxirane has been carried out to afford the hydroxylamine (13). Table 3 contains the results of analysis of 13 C NMR spectra for the urea (10) and the sulfonamides (14, 15) whose syntheses were described in Ref.…”

“…There is no band at 850-845 cm ‫1מ‬ characteristic of epoxynorbornane in its IR spectrum [11][12][13], and there is an absorption peak in the region 3304 cm ‫1מ‬ . The signals in the NMR spectrum have been assigned using a two-dimensional spectrum (COSY-experiment) and by comparison with the spectrum of exo-2-hydroxy-4-oxatricyclo[4.2.1.0 3,7 ]nonane (7) recorded earlier [2d].…”

Azabrendanes. I. Synthesis, structure and spectral parameters of N-(arylsulfonyl)-exo-2-hydroxy-4-azatricyclo[4.2.1.03,7]nonanes

“…On the contrary, the use of deuteroacetone makes the assignment of the signals for the weakfield protons H 2 , H 3 , and H 5 more complicated. In the 13 C NMR spectra of compounds (8b, 8h), there are no signals for the epoxy ring carbons in the region d ‫ס‬ 49-51, typical of epoxynorbornanes [16].…”