19172-64-6

Upstream product

• 98-88-4 benzoyl chloride 
• 622-30-0 N-benzyl hydroxylalmine 
• 959-32-0 N-(benzoyloxy)benzamide 
• 100-51-6 benzyl alcohol 
• 22687-11-2 salicylaldehyde-(N-benzyl oxime ) 
• 100-46-9 benzylamine 
• 94-36-0 dibenzoyl peroxide 
• 3376-26-9 N-Benzylidenebenzylamine N-oxide 
• 24850-33-7 allyltributylstanane 
• 90504-38-4 N-benzyl-O-benzoylhydroxylamine hydrochloride 

Downstream Products

• 7339-99-3 N-benzylbenzohydroxamic acid 

Relevant academic research and scientific papers

Nucleophilic Addition to Nitrones Using a Flow Microreactor

Nucleophilic addition reactions of soft carbon nucleophiles to nitrones in a flow microreactor are reported for the first time. Under microflow conditions at 30 to 0 °C, a range of nitrones can be efficiently transformed into the corresponding oxyiminium ions by reaction with either acyl halides or trialkylsilyl triflates. These can subsequently undergo the addition of nucleophiles including allyltributylstannane, ketene methyl tert-butyldimethylsilyl acetal, and N-silyl ketene imines to afford the corresponding adducts in high yields; such reactions at a similar temperature under batch conditions resulted in lower yields because of undesired side reactions.

Asymmetric synthesis of β-amino acids by addition of chiral enolates to nitrones via N-acyloxyiminium ions

N-Acyloxyiminium ions, generated by the reaction of nitrones with acyl halides, are highly reactive species and undergo facile reaction with a wide range of nucleophiles, such as ketene silyl acetals, titanium(IV) and boron enolates, hydrido- and allyltin(IV) reagents, and alkynyltitanium(IV) reagents, to give α-substituted amine derivatives. Optically active β-amino acids can be prepared by the reaction of N-acyloxyiminium ions with both boron and titanium(IV) enolates bearing chiral auxiliaries. Reversal of diastereoselectivity was observed by the reactions of the boron and titanium(IV) enolates. Using these reactions, all of the four stereoisomers of α-methyl-β-phenylalanines, for example, can be prepared highly diastereoselectively. Cyclic N-acyloxyiminium ions are useful for the asymmetric synthesis of pyrrolidine and piperidine alkaloids; (5R,8R,8aS)-5-cyano-8-methylindolizidine, which is a common key intermediate for synthesis of 5-substituted 8-methylindolizidines, was prepared selectively.

SYNTHESIS of NOVEL N-(PRIMARY)ALKYLHYDROXAMIC ACIDS

Synthesis of N-primary alkylhydroxamic acids is described in this paper by benzoyloxylation (benzoyl peroxide) of n-alkylamine and modification of the usual reaction conditions to stabilise the N-alkyl-O-benzoylhydroxylamine as the hydrochloride; this cir