Ae Aliev

Synthesis and certain transformations of γ-nitrosoalcohols

The γ-nitrosoalcohols (II), (XII), and (IX), respectively, have been synthesized by acid-catalyzed hydrolysis of 2-alkoxyisoxazolidines (I), (Xa, b), (Xla, b), and 3-(dimethoxyamino)-3-trifluoromethylbutanol-1 (VIII). The nitrosoalcohol (II) readily rearranges into the oxime (III), and (XII) is converted into the diol (XIII) by oxidation with atmospheric O2 and denitrosation. For (IX) and (XII) ring-chain tautomerism with formation of 2-hydroxyisoxazolidines could not be detected by PMR spectroscopy.

α,ω-Bis-N-aziridinoalkanes

By reactions of α,ω-diamines with 1,2-dihaloethanes there were synthesized α,ω-bis-N-aziridinoalkanes (la-g) and bis-N-aziridinoethyl ether (II). From 1,3-diaminopropane and dichloroethane bis-aziridine (III) was isolated in addition to (Ia). NMR spectra of the products were studied.

NMR spectral parameters of 1-chloroaziridine

l-Chloroaziridine is a classical case of hindered nitrogen inversion. Doubt has been cast on the PMR data obtained for this compound (3Jtran s = 2.54, 2j = -1.72 Hz) [i] since these coupling constants are significantly less than for l-chloro-2-methylaziridine [2] and other aziridines [3]. We obtained the following parameters by analyzing the PMR spectra at 400 MHz in CDCI 3 using the PANIC iteration program. These parameters differ significantly from those obtained by Pauelsen and Greve [i].