29195-01-5

Upstream product

• 350798-25-3 formic acid-(N,N'-dimethyl-N'-phenyl-hydrazide) 
• 38604-67-0 N'-methyl-N'-phenylformohydrazide 
• 74-88-4 methyl iodide 
• 7647-01-0 hydrogenchloride 
• 917-54-4 methyllithium 
• 52144-59-9 (Z)-(tert-butylsulfanyl)(phenyl)diazene 
• 618-40-6 1-Methyl-1-phenylhydrazine 
• 59986-06-0 N-methyl-N-phenylaminotriphenylphosphoranimine 
• 38435-93-7 propionic acid N_.N'-dimethyl-N'-phenylhydrazide 

Downstream Products

• 38435-93-7 propionic acid N_.N'-dimethyl-N'-phenylhydrazide 
• 1170697-35-4 C₁₀H₁₁⁽²⁾H₃N₂O 
• 350798-25-3 formic acid-(N,N'-dimethyl-N'-phenyl-hydrazide) 
• 15754-28-6 2-methyl-1-methylene-2-phenylhydrazine 
• 76579-56-1 N,N,N'-trimethyl-N'-phenylhydrazine 
• 69277-01-6 N¹,N²-Dimethyl-N²-phenylformohydrazidphenylsulfonylimid 
• 1170697-26-3 benzoic acid N,N'-dimethyl-N'-phenylhydrazide 

Relevant academic research and scientific papers

Photoinduced cleavage of N-N bonds of aromatic hydrazines and hydrazides by visible light

A photocatalytic system involving [Ru(bpyrz)(PFH, visible light, and air has been developed for cleavage of the N-N bonds of hydrazines and hydrazides. This catalytic system is generally effective for N,N-disubstituted hydrazine and hydrazide derivatives, including arylhydrazides, N-alkyl-N-arylhydrazines, and N,N-diarylhydrazines. The utility of this cleavage reaction has been demonstrated by synthesizing a variety of secondary aromatic amines. Georg Thieme Verlag Stuttgart ? New York.

Synthesis of indoles via alkylidenation of acyl hydrazides

Indoles have been synthesised via alkylidenation of acyl phenylhydrazides using phosphoranes and the Petasis reagent, followed by in situ thermal rearrangement of the product enehydrazines. The Petasis reagent provides an essentially neutral equivalent of the [acid-catalysed] Fischer indole synthesis, but with acyl phenylhydrazides as starting substrates. Alkylidene triphenylphosphoranes convert aroyl phenylhydrazides to indoles, but acyl phenylhydrazides derived from aliphatic carboxylic acids undergo a Brunner reaction to form indolin-2-ones.

A general procedure to selectively prepare N-alkylanilines by an unexpected reaction of (Z)-(tert-butylsulfanyl)(aryl)diazenes with alkyllithium reagents

A general procedure has been set up to prepare, selectively, the N-monoalkylanilines 7, reacting (Z)-(tert-butylsulfanyl)(aryl)diazenes 3 with alkyllithium 6 (MeLi, BuLi, s-BuLi, n-C6H13Li). The reactions were carried out in anhydrous diethyl ether at 0°C or - 78°C, depending on the reagent 6, and then at room temperature. In optimal conditions the yields of the pure products 7 (uncontaminated by dialkylation products) were from good to excellent: for 38 considered examples, 34 were positive with yields varying between 61percent and 91percent (average yield 78percent). Collateral proofs were carried out to support a hypothesized reaction mechanism.

Anionic [3,3], [2,3] and [1,2] rearrangements of aliphatic and aromatic acyl hydrazines with N-N bond cleavage

N-Acyl-N'-phenylhydrazines rearrange under basic conditions to afford α-aminophenylacetamides. This reaction can be rationalized in terms of [3,3] sigmatropic shifts of enolized intermediates. The Sommelet-Hauser-type and Stevens-type rearrangements of both aromatic and aliphatic acylhydrazines compete with the [3,3] rearrangement.