32818-95-4

Upstream product

• 7400-27-3 tertbutylhydrazine hydrochloride 
• 100-52-7 benzaldehyde 
• 32064-67-8 tert-butylhydrazine 

Downstream Products

• 1674-37-9 n-octanophenone 
• 94287-35-1 4-tert-Butylazo-3-methyl-4-phenyl-butyric acid methyl ester 
• 451-40-1 phenyl benzyl ketone 
• 24398-53-6 benzophenone-tert-butylhydrazone 
• 119-61-9 benzophenone 
• 7315-67-5 3-methyl-4-oxo-4-phenylbutanoic acid 
• 1154241-22-1 1-(tert-butyl)-3,5-diphenyl-1H-pyrazole 
• 725-12-2 2,5-bis-(phenyl)-1,3,4-oxadiazole 
• 4046-03-1 2-methyl-5-phenyl-[1,3,4]oxadiazole 
• 1874-39-1 2-(3-methylphenyl)-5-phenyl-1,3,4-oxadiazole 
• 1874-47-1 2-(4-methylphenyl)-5-phenyl-1,3,4-oxadiazole 
• 17064-48-1 2-(4-(tert-butyl)phenyl)-5-phenyl-1,3,4-oxadiazole 
• 825-56-9 2-phenyl-1,3,4-oxadiazole 

Relevant academic research and scientific papers

Mn(III)-mediated phosphinoylation of aldehyde hydrazones: Direct “one-pot” synthesis of α-iminophosphine oxides from aldehydes

A “one-pot” strategy for the straightforward Mn(III)-mediated phosphinoylation of aldehyde hydrazones with diphenylphosphine oxide to furnish α-iminophosphine oxides is described. This mild and practical method allows the direct use of aldehydes as substrates in one pot to generate the hydrazones, which are then engaged “in situ” by the phosphorus reagent in the presence of Mn(OAc)3 oxidant. Thus, the requisite isolation of the hydrazones is not needed in this operation. Conducted mechanistic experiments implicate a pathway involving phosphorus-centered radicals.

Radical Addition of Hydrazones by α-Bromo Ketones to Prepare 1,3,5-Trisubstituted Pyrazoles via Visible Light Catalysis

A novel efficient tandem reaction of hydrazones and α-bromo ketones is reported for the preparation of 1,3,5-trisubstituted pyrazoles by visible light catalysis. In this system, the monosubstituted hydrazones show wonderful reaction activity with alkyl radicals, generated from α-bromo ketones. A radical addition followed by intramolecular cyclization affords the important pyrazole skeleton in good to excellent yields. This efficient strategy under mild conditions with wide group tolerance provides a potential approach to the 1,3,5-trisubstituted pyrazoles.

Palladium-catalyzed synthesis of aryl ketones by coupling of aryl bromides with an acyl anion equivalent

Palladium-catalyzed couplings of aryl bromides with N-tert-butylhydrazones as acyl anion equivalents to form aryl ketones are reported. The coupling process occurs at the C-position of hydrazones to form N-tert-butyl azo compounds. Isomerization of these azo compounds to the corresponding hydrazones, followed by hydrolysis, gave the desired mixed alkyl aryl ketones. The selectivity of C- versus N-arylation was strongly influenced by the substituent on nitrogen. Arylation at carbon occurred with N-tert-butylhydrazones, whereas N-arylation occurred with N-arylhydrazones. The arylation of hydrazones containing primary and secondary alkyl groups, as well as aryl groups, gave the desired ketones in good yields after hydrolysis. Functional groups on the aromatic ring, such as alkoxy, cyano, trifluoromethyl, carboalkoxy, carbamoyl, and keto groups, were tolerated. This reaction likely occurs by C-C bond-forming reductive elimination from an intermediate containing an η1-diazaallyl ligand. Copyright

AZO ANIONS IN SYNTHESIS. PT 1. t-BUTYLHYDRAZONES AS ACYL-ANION EQUIVALENTS

The lithium salts of aldehyde t-butylhydrazones react with electrophiles (aldehydes, ketones, alkyl halides, crotonates) to form C-trapped t-butylazo-compounds; tautomerisation and hydrolysis gave α-hydroxy ketones, ketones, and γ-keto esters in good yield, thereby providing a convenient new acyl-anion equivalent.Reaction of these lithium salts with aldehydes and ketones, followed by elimination provided a new route to azo alkenes.