188818-01-1Relevant articles and documents
Mechanistic considerations for the consecutive cyclization of 2,3-dibromopropylamine hydrobromide giving a strained molecule, 1-azabicyclo[1.1.0]butane
Hayashi, Kazuhiko,Ikee, Yoshifumi,Goto, Satoru,Shiro, Motoo,Nagao, Yoshimitsu
, p. 89 - 94 (2004)
The effective formation of 1-azabicyclo[1.1.0]butane (2) by treatment of 2,3-dibromopropylamine hydrobromide (1) with n-BuLi could be understood considering a rational reaction pathway via both transition states 10 and 19 based on the intramolecular Br...
Coupling of 1-alkyl-2-(bromomethyl)aziridines with lithium dialkylcuprates towards 1,2-dialkylaziridines
D'Hooghe, Matthias,Rottiers, Mario,Jolie, Robrecht,De Kimpe, Norbert
, p. 931 - 934 (2007/10/03)
The reactivity of 1-alkyl-2-(bromomethyl)aziridines with respect to lithium dialkylcuprates (Gilman reagents) has been evaluated for the first time, pointing to the conclusion that these substrates can be applied successfully as synthetic equivalents for
A new synthesis of 2-methyleneaziridines
De Kimpe, Norbert,De Smaele, Dirk,Sakonyi, Zsolt
, p. 2448 - 2452 (2007/10/03)
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.
