156697-63-1

Upstream product

• 156697-64-2 (E)-N-(4-methylbenzylidene)prop-2-en-1-amine 
• 104-87-0 4-methyl-benzaldehyde 
• 80975-83-3 N-(4-methylbenzylidene)prop-2-en-1-amine 
• 188818-02-2 N-(4-methylbenzylidene)-2,3-dibromopropylamine 
• 156697-67-5 (2,3-Dibromo-propyl)-[1-p-tolyl-meth-(E)-ylidene]-amine 

Downstream Products

• 86926-54-7 N-(4-methylbenzyl)prop-2-en-1-amine 
• 685891-60-5 N-benzyl-N-(2,3-dibromopropyl)-N-((4-methylphenyl)methyl)amine 
• 952024-07-6 2-(2-cyanoethyl)-1-[(4-methylphenyl)methyl]aziridine 
• 883199-66-4 N,N-di(4-methylbenzyl)-N-[2-bromo-3-(4-chlorophenoxy)propyl]amine 
• 1005340-37-3 2-[(4-methylbenzyl)amino]pentanedinitrile 
• 897440-36-7 2-(cyanomethyl)-1-(4-methylbenzyl)aziridine 

Relevant academic research and scientific papers

A new synthesis of 2-methyleneaziridines

A new synthetic route leading to 2-methyleneaziridines has been developed by base-induced 1,2-dehydrobromination of 2-(bromomethyl)aziridines. Several base-solvent pairs did not lead to 2-methyleneaziridines. Only potassium tert-butoxide in tetrahydrofuran afforded 2-methyleneaziridines in competition with the substitution products, i.e. 2-(tert-butoxymethyl)aziridines. Various attempted functionalizations of 1-(arylmethyl)-2-methyleneaziridines failed, but they proved to be excellent substrates for the synthesis of β-lactam derivatives, i.e. 1-(arylmethyl)-2-iminoazetidines, through ring expansion with azides carrying electron-withdrawing substituents.

Sonochemical Cleavage of 2-(Bromomethyl)aziridines by a Zinc-Copper Couple

1-Alkyl- and 1-arylmethyl-2-(bromomethyl)aziridines are readily cleaved by the sonochemical zinc-copper couple in aqueous methanol at room temp. to afford allylamines.