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Potassium N ‐Iodo p ‐Toluenesulfonamide (TsNIK, Iodamine‐T): A New Reagent for the Oxidation of Hydrazones to Diazo Compounds
Author(s) -
Nicolle Simon M.,
Moody Christopher J.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304656
Subject(s) - diazo , reagent , hydrazone , chemistry , yield (engineering) , potassium , organic chemistry , medicinal chemistry , metallurgy , materials science
A new reagent for the oxidation of hydrazones to diazo compounds is described. N ‐Iodo p ‐toluenesulfonamide (TsNIK, iodamine‐T) allows the preparation of α‐diazoesters, α‐diazoamides, α‐diazoketones and α‐diazophosphonates in good yield and in high purity after a simple extractive work‐up. α‐Diazoesters were also obtained in high yield from the corresponding ketones through a one‐pot process of hydrazone formation/oxidation.