Comments on a facile conversion of epoxides to halohydrins with elemental halogen using isonicotinic hydrazide (isoniazide) as a new catalyst—a reinvestigation
Author:
Publisher
Elsevier BV
Subject
Physical and Theoretical Chemistry,Process Chemistry and Technology,Catalysis
Reference22 articles.
1. A facile conversion of epoxides to halohydrins with elemental halogen using isonicotinic hydrazide (isoniazide) as a new catalyst
2. The halogenations of isonicotinic hydrazide and the oxidations of isonicotinic hydrazide by halogens were not described in the literature. However, we found some literature precedents concerning the reaction of some aromatic and aliphatic hydrazides with halogens, according to them the reaction of hydrazides with chlorine, bromine or iodine, gave mainly oxidation products, which could be derived from acyldiazonium salts. For example: T. Curtius, J. Prakt. Chem. 50 (1894) 275–294.
3. 21. Th. Curtius: Hydrazide und Azide organischer Säuren II. Abhandlung. Ueber Benzhydrazid
4. Die titrimetrische Bestimmung von Hydrazin und die Verwendung von Hydrazinsulfat zur Titerstellung der Jodlösung
5. A closely related chemistry of substituted hydrazines were extensively reported in the literature. For example, the reactions of arylhydrazine with chlorine or bromine gave a mixture of oxidized and halogenated products: F.D. Chattaway, G.D. Hodgson, J. Chem. Soc. (1916) 582–587.
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1. Kinetic and thermodynamic study of inter- and intramolecular proton transfer in N ′-acetyl formohydrazide tautomers;International Journal of Quantum Chemistry;2010-10-06
2. DFT study of N′-acetyl formohydrazide isomers;Journal of Molecular Structure: THEOCHEM;2010-08
3. Unexpected Highly Efficient Ring-Opening of Aziridines or Epoxides with Iodine Promoted by Thiophenol;Synlett;2006-09
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