57139-40-9

Upstream product

• 613-92-3 N-hydroxybenzenecarboximidamide 
• 98-88-4 benzoyl chloride 
• 2446-51-7 N-methoxybenzamide 
• 4424-16-2 O-methyl-benzamidoxime 

Downstream Products

• 2446-51-7 N-methoxybenzamide 
• 57598-91-1 methyl (Z)-O-methylbenzothiohydroximate 
• 253663-21-7 (Z)-N-methoxybenzenecarboximidoyl fluoride 
• 1224174-90-6 O-methylbenzohydroximoyl azide 
• 1429897-19-7 (Z)-3-(3-hydroxyphenyl)-1-phenylprop-2-yn-1-one O-methyl oxime 
• 1429897-18-6 (Z)-3-cyclopropyl-1-phenylprop-2-yn-1-one O-methyl oxime 
• 1429897-17-5 (Z)-4-methyl-1-phenylpent-4-en-2-yn-1-one O-methyl oxime 
• 42449-49-0 (Z)-4-methylbenzophenone O-methyl oxime 
• 3376-34-9 benzophenone oxime methyl ether 
• 100-47-0 benzonitrile 
• 253663-27-3 (E)-N-methoxybenzenecarboximidoyl fluoride 
• 57598-90-0 methyl (E)-O-methylbenzothiohydroximate 

Relevant academic research and scientific papers

Stereospecific Suzuki, Sonogashira, and Negishi coupling reactions of N-alkoxyimidoyl iodides and bromides

A high-yielding stereospecific route to the synthesis of single geometric isomers of diaryl oxime ethers through Suzuki coupling of N-alkoxyimidoyl iodides is described. This reaction occurs with complete retention of the imidoyl halide geometry to give single E- or Z-isomers of diaryl oxime ethers. The Sonogashira coupling of N-alkoxyimidoyl iodides and bromides with a wide variety of terminal alkynes to afford single geometric isomers of aryl alkynyl oxime ethers has also been developed. Several of these reactions proceed through copper-free conditions. The Negishi coupling of N-alkoxyimidoyl halides is introduced. The E and Z configurations of nine Suzuki-coupling products and two Sonogashira-coupling products were confirmed by X-ray crystallography.

Imino 1,2-Wittig rearrangement of hydroximates and its application to synthesis of cytoxazone

The imino 1,2-Wittig rearrangement of hydroximates provides a novel method for the construction of 2-hydroxyoxime ethers. Upon treatment with LDA, Z-hydroximates smoothly underwent stereoselective rearrangement to give Z-2-hydroxyoxime ethers in good yield, which were converted into amino alcohols. On the other hand, the rearrangement of E-hydroximates gave a mixture of E- and Z-2-hydroxyoxime ethers. This method was successfully applied to a practical synthesis of cytoxazone.

Mechanism of Solvolysis Reactions of O-Methylbenzohydroximoyl Halides. Stereoelectronic Control in Formation of and Nucleophilic Addition to Nitrilium Ions

The hydrolysis reactions of the Z and E isomers of O-methylbenzohydroximoyl chloride (3a and 2, respectively) have been investigated. The first-order rate constant for the hydrolysis of 3a (1) shows common-ion rate depression, (2) decreases with decreasin