Imines and their N-substituted derivatives: hydrazones and other N,N-derivatives including diazo compounds

Elliott, Mark C. ORCID: https://orcid.org/0000-0003-0132-0818 and Ju, Minsoo 2026. Imines and their N-substituted derivatives: hydrazones and other N,N-derivatives including diazo compounds. Elsevier Reference Collection in Chemistry, Molecular Sciences and Chemical Engineering, Elsevier, (10.1016/b978-0-443-31482-7.00093-x)

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Abstract

Methods for the formation of diazo compounds, hydrazones, and imines substituted with a heteroatom at nitrogen are reviewed. For the formation of hydrazones, the reaction of a carbonyl compound with a hydrazine remains the most popular method, although there has been a significant increase in the reports of functionalization of hydrazones, both at the hydrazone carbon and the α-carbon. Metallated imines are prepared by a variety of methods, depending on the choice of metal. N-Lithiated imines are generally prepared by the addition of organolithium reagents to nitriles, although these compounds are seldom isolated. N-Silylimines are most conveniently prepared by the addition of a bis-silylamine to a carbonyl compound or TMS-azide to an N-heterocyclic carbene. These two classes of substituted imines have been used to prepare a range of other heteroatom-substituted imines by substitution of either lithium or silicon. Diazo compounds are most commonly prepared by diazo transfer to a methylene group flanked by one or more electron-withdrawing groups. Sulfonyl azides are widely used to achieve this transformation, although a range of reagents and other modifications have been used in individual cases. In recent years, the versatility of the diazo group has been demonstrated by a number of new reactions, which feature elaboration of diazo compounds either at the diazo-carbon or elsewhere. Oxidation of hydrazones and Bamford–Stevens reaction of sulfonylhydrazones have also been used to prepare diazo compounds.

Item Type:	Book Section
Date Type:	Publication
Status:	Published
Schools:	Schools > Physical, Chemical & Environmental Sciences
Additional Information:	This is an update of M.C. Elliott, 3.12 - Imines and Their N-Substituted Derivatives: Hydrazones and Other N,N-Derivatives Including Diazo Compounds, Editor(s): Alan R. Katritzky, Richard J.K. Taylor, Comprehensive Organic Functional Group Transformations II, Elsevier, 2005, Pages 469–523, ISBN 9780080446554, https://doi.org/10.1016/B0-08-044655-8/00057-X. See ORCA record https://orca.cardiff.ac.uk/id/eprint/39946/
Publisher:	Elsevier
ISBN:	9780124095472
Last Modified:	01 Sep 2026 09:30
URI:	https://orca.cardiff.ac.uk/id/eprint/189253

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