Carbon–carbon double bond isomerization in heterocyclic hydrazine derivatives

Double bond isomerization by in situ generated ruthenium hydride catalyst in 6- to 9-membered hydrazine heterocycles including an endocyclic N–N bond was investigated. Based on the results of the experiments, a conclusion was made that the generation of resonance-stabilized enehydrazides is generall...

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Published inChemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 54; no. 5; pp. 572 - 575
Main Authors Ilisson, Mihkel, Tomson, Kristjan, Tamm, Tarmo, Mäeorg, Uno
Format Journal Article
LanguageEnglish
Published New York Springer US 01.05.2018
Springer Nature
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Springer Nature B.V
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Summary:Double bond isomerization by in situ generated ruthenium hydride catalyst in 6- to 9-membered hydrazine heterocycles including an endocyclic N–N bond was investigated. Based on the results of the experiments, a conclusion was made that the generation of resonance-stabilized enehydrazides is generally favored, but in some cases, the reaction pathway is presumably also highly dependent of steric interactions. With the current method, two novel enehydrazide heterocycles and one enehydrazine heterocycle were produced and characterized.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-018-2308-9