BASE INDUCED REACTION OF AN AZETIDIN-2-ONE: FORMATION OF A NOVEL [1,4]-DIAZEPINEDIONE

REFERENCES

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• In the proton NMR spectrum, in addition to the resonances for the 6-phenylhexyl chain, four other reasonance signals were present. These consisted of a doublet at δ3.93 (2H, J = 5.0 Hz), a double doublet at δ5.10 (1H, dd, J = 8.3 Hz, J = 1.9 Hz), a broad multiplet at δ5.77 (1H) and a second double doublet at δ6.88 (1H, J = 8.3 Hz, J = 6.0 Hz). Addition of D2O to the NMR solution resulted in the complete disappearance of the broad multiplet at δ5.77 (assigned to the N-H proton in 2) and also simplified the observed coupling multiciplity of the remaining signals. Thus, the doublet at δ3.93 collapsed to a singlet and both of the remaining double doublets collapsed to clean doublets (J = 8.4 Hz). The reasonances of the phenylhexyl group were not affected by D2O addition. A J-modulated carbon spectrum of 2 confirmed the presence of the methine bearing carbons at C5 and C6 with a downfield shift being observed for C6 (145.5 ppm) relative to C5 (96.3 ppm) consistent with its attachment to nitrogen compared to carbon for C5. The presence of the two carbonyl carbon atoms was also confirmed by the resonance signals at 167.9 and 166.1 ppm
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