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- W2078169416 abstract "A new bicyclic system, 3,7-diazabicyclo[4.1.0]heptane, has been prepared from 3-(ethoxycarbonyl)-7,3-oxazabicyclo[4.1.0]heptane by reaction with sodium azide and reduction of the resulting tosyloxy azide with lithium aluminum hydride. The molecule can exist in four stereoisomeric half-chairs, depending on the configuration of the two nitrogen atoms. Half-chair ring reversal and piperidine nitrogen inversion are fast on the NMR time scale at all observed temperatures. Inversion of the secondary aziridine nitrogen becomes slow as the temperature is lowered (Tc= −10°C). Complete analysis of the 1H spectrum was possible with the 1,5,5-trideuteriated analog. At slow exchange, two aziridine invertomers are present with an exo/endo ratio of approximately 0.7 in toluene-d8, 0.7 in CH2Cl2 and 1.7 in CHCl3/CH2Cl2. The free energy of activation for nitrogen inversion is 13.2 kcal mol−1 at −10°C in CHCl3/CH2Cl2." @default.
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- W2078169416 date "1983-09-01" @default.
- W2078169416 modified "2023-09-22" @default.
- W2078169416 title "Synthesis and dynamic NMR studies of the 3,7-diazabicyclo[4.1.0]heptane system" @default.
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- W2078169416 doi "https://doi.org/10.1002/omr.1270210904" @default.
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