Russian Chemical Bulletin p. 1316 - 1322 (1999)
Update date:2022-08-05
Topics:
Tomilov
Kostyuchenko
Shulishov
Averkiev
Antipin
Nefedov
Oxidation of N-aminophthalimide with lead tetraacetate in the presence of spiro(1-pyrazolinecyclopropanes) at temperature from -20 °C to -30 °C resulted in the formal generation of phthalimidonitrene followed by its addition at the N=N bond of the pyrazoline ring to form 5(3)-substituted N-{spiro[1-pyrazolinio-3(5),1′-cyclopropane]}-N-phthalimidoamides (azimines), whose regioisomeric compositions were determined to a large extent by the nature of the substitueras in the pyrazoline ring. The structures of phthalimidoazimines were established based on the NMR spectra and X-ray diffraction data. Thermal conversions of the resulting adducts, which proceeded either with retention or with opening of the spiro-fused cyclopropane ring, were studied.
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Doi:10.1016/S0022-328X(99)00385-X
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