Reaction Of Methylhydrazine Research Articles

Structural revision of products resulting from the reaction of methylhydrazine with acridin-9-yl isothiocyanate due to unexpected acridinyl migration and further reactions

The reaction of methyl acridin-9-ylthiosemicarbazide under basic conditions with methyl bromoacetate resulted in a 1,3-thiazolin-4-one structure as provided by X-ray crystallography. The structure forced a re-evaluation of the reactant methyl acridin-9-ylthiosemicarbazide, originally thought to be 2-methyl 4-acridin-9-ylthiosemicarbazide based on synthetic expectations, but which when examined by X-ray crystallography was found to be in fact the isomeric 2-methyl 1-acridin-9-ylthiosemicarbazide resulting from rearrangement via a spiro form which it is in equilibrium with in solution. The product resulting from reaction with methyl iodide was also studied and the previously reported semicarbazide produced by reaction with MNO was re-examined. In both cases, the 1,2 isomer rather than the 2,4 isomer was found to be present based on the sign of the 3 JCH3,N11 coupling. Full characterization of the compounds was rendered by 1 H, 13 C, and 15 N solution-state NMR, and in the solid state, by both 13 C and 15 N NMR.

Transition Metal Chemistry of Main Group Hydrazides. 17. Triphosphine derived from phosphanyl hydrazide as a building block for hetero trimetallic compounds. Synthesis and coordination chemistry of ((Me2P)2NN(Me)(PMe2))

AbstractThe new triphosphine (Me2P)2NN(Me)(PMe2) (1), has been synthesized in pure form by the reaction of methylhydrazine with dimethylchlorophosphine in the presence of triethylamine. This triphosphine represents a bridge between phosphinoamine (>PN(R)P<) and phosphanyl hydrazide (>PN(R)N(R)P<) backbones. Reaction of 1 with cis‐[W(CO)4(NHC5H10)2] proceeds via two coordination modes to give four‐membered MPNP and five‐membered MPNNP metallacyclic frameworks. The tungsten complex cis‐[W(CO)4{(Me2P)2NN(Me)(PMe2)}] (2) possessing an uncoordinated phosphine moiety to prepare multimetallic organometallic compounds. For example, reactions of 2 with PdCl2(PhCN)2 and PtCl2(COD) produced the trimetallic complexes consisting of W(0)Pt(II) and W(0)Pd(II) centers respectively in good yields. The different isomers of these trinuclear complexes have been clearly identified by 31P NMR spectroscopy.

Methyl hydrazine as a building block for a bridge between phosphinoamine [R2P–N(R)–PR2] and phosphorus hydrazide [R2P–N(R)–N(R)–PR2]. Synthesis and coordination chemistry of a novel triphosphine [(Me2P)2N–N(Me)(PMe2)

The reaction of methylhydrazine with dimethylchlorophosphine in the presence of triethylamine affords the new triphosphine (Me2P)2N–N(Me)(PMe2)1 in near quantitative yields, which represents a bridge between phosphinoamine [>P–N(R)–P P–N(R)–N(R)–P<]backbones; reaction of 1 with cis-[W(CO)4(NHC5H10)2] proceeds via two coordination modes to give M–P–N–P and M–P–N–N–P metallacyclic frameworks; the structure of the phosphinoamine coordinated part of 1 has been demonstrated by X-ray crystallographic investigation of 2.

ChemInform Abstract: Reaction of Methylhydrazine with Dimethyl Chlorothiophosphate.

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Reaction of methylhydrazine with dimethyl chlorothiophosphate

The reaction of 2 equivalents of methylhydrazine with 1 equivalent of (MeO)2P(S)Cl at 0 °C produced the phosphorus hydrazide (MeO)2P(S)NMeNH21 in good yield. However, at 25 °C a mixture of three products was obtained according to 1H and 31P NMR spectra. The pure individual components were separated by column chromatography. Proton and 31P NMR analysis revealed them to be 1, (MeO)2P(S)(NMeNH)(S)P(OMe)22 and (MeO)2P(S)NHNHMe 3. During the chromatographic separation of 1–3 another component was also eluted in 5–8% yield, 1H, 31P NMR and FAB mass spectrometric analysis of which indicated it to be (MeO)2P(S)(NMeNH)(O)P(OMe)Me4. New synthetic strategies to produce 2 in good yields are also described.

ChemInform Abstract: Formation of N‐Methylporphyrin by Reaction of Methylhydrazine with Cytochrome P‐450 Model.

ChemInform Abstract: Formation of N‐Methylporphyrin by Reaction of Methylhydrazine with Cytochrome P‐450 Model.

Regioselective addition of hydrazines to allenylacetylenes ? Convenient route to 3(5)-methyl-5(3)-substituted pyrazoles

It is shown that hydrazine hydrate, methylhydrazine, and phenylhydrazine add smoothly and regioselectively to allenylacetylenes to give 3(5)-methyl-5(3)-sub-stituted pyrazoles. In addition to the principal process, isomerization of allenylacetylenes to methyldiacetylenes, and the degree of which depends on the structure of the substrate, is observed in the reaction of methylhydrazine in an aqueous alcohol medium.

Notiz über die Reaktion von Methylhydrazin mit N‐Cyano‐azomethinen. Abhängigkeit des Reaktionsverlaufs von der Natur der Abgangsgruppe

The reaction of methylhydrazine with N‐cyanoazomethines 1 containing a thioalkyl leaving group yields the 3‐amino‐1,2,4‐triazole derivatives 2, whereas the N‐cyanoazomethines 1 containing an alkoxy leaving group give the isomeric 5‐amino‐1,2,4‐triazoles 3. The yields are excellent and the position selectivity is high. The structures of the 1,2,4‐triazole derivatives were determined with the aid of proton‐coupled 13C‐NMR. spectra.

Reaction of alkylhydrazines. 3. Reaction of methylhydrazine and 1,1-dimethylhydrazine with cis- and trans-cyclohexane-1,2-dicarboxylic anhydrides. Products and reaction sequence

Reaction of alkylhydrazines. 3. Reaction of methylhydrazine and 1,1-dimethylhydrazine with cis- and trans-cyclohexane-1,2-dicarboxylic anhydrides. Products and reaction sequence

Formation of Urazole Ring from Monoalkylhydrazine and Carbon Monoxide by Selenium

Abstract The reaction of monomethylhydrazine with carbon monoxide in the presence of selenium gave a monoselenocarbazic acid salt of methylhydrazine (I), and the reaction of methylhydrazine with a mixture gas of carbon monoxide and oxygen in the presence of I at room temperature gave 4-methylamino-l-methylurazole (III). The structure of III was determined by 1H NMR and FT 13C NMR.

Alkylidenebis‐1‐methyl‐2‐alkylidenehydrazines as intermediates in the reaction of methylhydrazine with aliphatic aldehydes

AbstractIt has been shown that heptylidenebis‐1‐methyl‐2‐heptylidenehydrazine (Va) is an intermediate in the reaction of methylhydrazine with heptanal. The bis‐compound (Va) reacts with methylhydrazine to give heptanal methylhydrazone (IIa), or with heptanal, in the presence of acid, to afford 5‐hexyl‐1‐methyl‐4‐pentyl‐2‐pyrazoline (Ia). The latter also results from the treatment of IIa with acid.