Yv. Tomilov et al., Formation and thermal decomposition of adducts of phthalimidonitrene with spiro(1-pyrazolinecyclopropanes), RUSS CHEM B, 48(7), 1999, pp. 1316-1322
Oxidation of N-aminophthalimide with lead tetraacetate in the presence of s
piro(1-pyrazolinecyclopropanes) at temperature from -20 degrees C to -30 de
grees 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)-substitut
ed N-{spiro[1-pyrazolinio-3(5),1'-cyclopropane]}-N-phthalimidoamides (azimi
nes), whose regioisomeric compositions were determined to a large extent by
the nature of the substituents in the pyrazoline ring. The structures of p
hthalimidoazimines were established based on the NMR spectra and X-ray diff
raction data. Thermal conversions of the resulting adducts, which proceeded
either with retention or with opening of the spiro-fused cyclopropane ring
, were studied.