Oxidation of hydrazones with iodine in the presence of base

A. Pross; S. Sternhell

doi:10.1071/CH9700989

Oxidation of hydrazones with iodine in the presence of base

A. Pross, S. Sternhell

Research output: Contribution to journal › Article › peer-review

117 Scopus citations

Abstract

The oxidation of 14 hydrazones with iodine in the presence of base (generally triethylamine) was investigated. The typical reaction products are mixtures of gem-diiodides and vinyl iodides obtained in total yields of 38-85%. The features of the reaction are consistent with a mechanism involving an intermediate iododiazonium salt and/or an iodocarbonium ion. The preparation and purification of hydrazones was investigated.

Original language	English
Pages (from-to)	989-1003
Number of pages	15
Journal	Australian Journal of Chemistry
Volume	23
Issue number	5
DOIs	https://doi.org/10.1071/CH9700989
State	Published - 1 Jan 1970
Externally published	Yes

ASJC Scopus subject areas

Chemistry (all)

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10.1071/CH9700989

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title = "Oxidation of hydrazones with iodine in the presence of base",

abstract = "The oxidation of 14 hydrazones with iodine in the presence of base (generally triethylamine) was investigated. The typical reaction products are mixtures of gem-diiodides and vinyl iodides obtained in total yields of 38-85%. The features of the reaction are consistent with a mechanism involving an intermediate iododiazonium salt and/or an iodocarbonium ion. The preparation and purification of hydrazones was investigated.",

author = "A. Pross and S. Sternhell",

note = "Funding Information: We wish to thank the Australian Research Grants Committee for funds for the purchase of the 100-MHz n.m.r. and mass spectrometers.",

year = "1970",

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N2 - The oxidation of 14 hydrazones with iodine in the presence of base (generally triethylamine) was investigated. The typical reaction products are mixtures of gem-diiodides and vinyl iodides obtained in total yields of 38-85%. The features of the reaction are consistent with a mechanism involving an intermediate iododiazonium salt and/or an iodocarbonium ion. The preparation and purification of hydrazones was investigated.

AB - The oxidation of 14 hydrazones with iodine in the presence of base (generally triethylamine) was investigated. The typical reaction products are mixtures of gem-diiodides and vinyl iodides obtained in total yields of 38-85%. The features of the reaction are consistent with a mechanism involving an intermediate iododiazonium salt and/or an iodocarbonium ion. The preparation and purification of hydrazones was investigated.

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Oxidation of hydrazones with iodine in the presence of base

Abstract

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