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Conversions of hydrazones to diazo compounds by n-butyllithium and azidotris(diethylamino)phosphonium bromide

✍ Scribed by Mark McGuiness; Harold Shechter

Book ID: 104251777
Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 87 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01443-0

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✦ Synopsis

Lithium hydrazonides, prepared by reactions of hydrazones with n-BuLi/hexane in THF at -78°C, are converted by azidotris(diethylamino)phosphonium bromide in THF at 0°C efficiently, rapidly, and safely to their corresponding diazo compounds along with tris(diethylamino)phosphorimine, nitrogen, and lithium bromide.

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Conversions of primary amines to azides

Conversions of primary amines to azides by n-butyllithium and azidotris(diethylamino)phosphonium bromide

✍ Stephen P Klump; Harold Shechter 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 90 KB

Lithium derivatives of varied aromatic, heterocyclic, aliphatic, and alicyclic primary amines react efficiently with azidotris(diethylamino)phosphonium bromide in THF at low temperatures to give azides, lithium bromide, nitrogen, and tris(diethylamino)phosphorimine.