Advantageous Syntheses of Diazo Compounds by Oxidation of Hydrazones with Lead Tetraacetate in Basic Environments
作者:Terrence L. Holton、Harold Schechter
DOI:10.1021/jo00120a013
日期:1995.7
Varied sensitive diazo compounds 3 are produced efficiently and safely in 3-6 g quantities by oxidation (eq 1) of hydrazones 1 at -78 degrees C with lead tetraacetate (2) in triethylamine/chloroform, N-methylmorpholine/dimethylformamide, tetramethylguanidine (8)/dimethylformamide, and tetramethylguanidine/methylene chloride, respectively, upon use of appropriate workup and handling techniques. New and improved nonhazardous procedures have been developed for preparing and handling hydrazones 1 from aldehydes and ketones in reactions with excess hydrazine.