136984-61-7

Upstream product

• 637-60-5 p-tolylhydrazine hydrochloride 
• 431-03-8 dimethylglyoxal 
• 2028-84-4 p-methylbenzenediazonium chloride 
• 1522-25-4 4-hydroxy-3-methylpent-3-en-2-one 
• 140244-83-3 (Z)-(4-methylphenyl)azo tert-butyl sulfide 
• 78-93-3 butanone 
• 57573-52-1 4-methylbenzene diazonium 

Downstream Products

• 209258-03-7 [PdCl(C₁₁H₁₃N₂O)(P(C₆H₅)3)2] 
• 209258-15-1 [Pd(C₁₁H₁₂N₂O)(P(C₆H₅)3)] 
• 24006-21-1 N-methyl-N-(4-tolyl)hydrazine 
• 5705-16-8 N-benzyl-N-(p-methylphenyl)hydrazine 

Relevant academic research and scientific papers

An easy access to 2-oxohydrazones via electrophilic α-p-tolylhydrazonylation of ketone enolates with tert-butyl p-tolylazo sulfide

The title reaction conveniently furnishes, as the sole or main products, α-(p-tolylhydrazono)ketones or their N-methylderivatives (H+ or MeI quenching of the final mixture, respectively). Although the method fails with ketones having a secondary alkyl group bonded to the carbonyl, yields are otherwise more than satisfactory and particular interest is attached to the hydrazonylation of the methyl group in methyl ketones.

Addition of Semidione Radicals to Arenediazonium Ions: Synthesis of 1,1-Diacyl-2-arylhydrazines

The α-dicarbonyl compounds 1 are selectively reduced to semidione radicals 2 by aqueous Ti3+, via inner-sphere electron transfer (ET).When an equimolar amount of an arenediazonium salt (3) is present, 2 adds to the nitrogen-nitrogen triple bond of 3 to afford the intermediate azo radical cation C, which, depending on the nature of the para substituent of the N-phenyl ring, undergoes rearrangement to a 1,1-diacyl-2-arylhydrazine (4) or preferentially reduction to a hydrazone (5).A mechanism that accounts for both the rearrangement and the substituent effects that are observed is proposed.