Abstract
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.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1563–1568, July, 1991.
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Rudchenko, V.F., Chervin, I.I., Aliev, A.É. et al. Synthesis and certain transformations of γ-nitrosoalcohols. Russ Chem Bull 40, 1380–1386 (1991). https://doi.org/10.1007/BF00961236
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DOI: https://doi.org/10.1007/BF00961236