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CARBON–CARBON DOUBLE BOND ISOMERIZATION IN HETEROCYCLIC HYDRAZINE DERIVATIVES

Mihkel Ilisson, Kristjan Tomson, Tarmo Tamm, Uno Mäeorg
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Abstract


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 resonancestabilized 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.


Keywords


heterocyclic chemistry; hydrazine derivatives; isomerization; homogeneous catalysis; enamides

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