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Is there Ring–Chain Tautomerism in γ-Nitrosoalkanols?

Vladimir Fedorovich Rudchenko 1
Vladimir Fedorovich Rudchenko
, 
Ivan Ivanovich Chervin 1
Ivan Ivanovich Chervin
, 
Remir Grigorevich Kostyanovsky 1
Remir Grigorevich Kostyanovsky
10.1070/MC1991v001n01ABEH000006
Published 1991-03-31
Communication , Volume 1, Issue 1, 9-10
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Rudchenko V. F., Chervin I. I., Kostyanovsky R. G. Is there Ring–Chain Tautomerism in γ-Nitrosoalkanols? // Mendeleev Communications. 1991. Vol. 1. No. 1. pp. 9-10.
GOST all authors (up to 50) Copy
Rudchenko V. F., Chervin I. I., Kostyanovsky R. G. Is there Ring–Chain Tautomerism in γ-Nitrosoalkanols? // Mendeleev Communications. 1991. Vol. 1. No. 1. pp. 9-10.
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TY - JOUR
DO - 10.1070/MC1991v001n01ABEH000006
UR - https://mendcomm.colab.ws/publications/10.1070/MC1991v001n01ABEH000006
TI - Is there Ring–Chain Tautomerism in γ-Nitrosoalkanols?
T2 - Mendeleev Communications
AU - Rudchenko, Vladimir Fedorovich
AU - Chervin, Ivan Ivanovich
AU - Kostyanovsky, Remir Grigorevich
PY - 1991
DA - 1991/03/31
PB - Mendeleev Communications
SP - 9-10
IS - 1
VL - 1
ER -
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@article{1991_Rudchenko,
author = {Vladimir Fedorovich Rudchenko and Ivan Ivanovich Chervin and Remir Grigorevich Kostyanovsky},
title = {Is there Ring–Chain Tautomerism in γ-Nitrosoalkanols?},
journal = {Mendeleev Communications},
year = {1991},
volume = {1},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1991v001n01ABEH000006},
number = {1},
pages = {9--10},
doi = {10.1070/MC1991v001n01ABEH000006}
}
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Rudchenko, Vladimir Fedorovich, et al. “Is there Ring–Chain Tautomerism in γ-Nitrosoalkanols?.” Mendeleev Communications, vol. 1, no. 1, Mar. 1991, pp. 9-10. https://mendcomm.colab.ws/publications/10.1070/MC1991v001n01ABEH000006.

Abstract

γ-Nitrosoalkanols 2, 6 and 8, obtained upon acid hydrolysis of 2-methoxyisoxazolidines 1 and 7 and of dimethoxyamine 5, respectively, do not display ring–chain tautomerism, i.e. formation of the corresponding 2-hydroxyisoxazolidines (‘heminitrosals’); nitrosoalkanol 2 smoothly rearranges to oxime 4, whilst compound 8 in MeOH gives diol 9, probably via aerial oxidation to the corresponding nitrite followed by denitrosation.

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