Mechanistic considerations for the consecutive cyclization of 2,3-dibromopropylamine hydrobromide giving a strained molecule, 1-azabicyclo[1.1.0]butane.
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...Li(+) coordination. A similar cyclization pathway starting from N-benzyl-3-bromopropylamine hydrochloride (17) to afford N-benzylazetidine (18) could also be postulated on the basis of a transition state 20 involving the intramolecular Br...Li(+) coordination.
Hayashi
Kazuhiko
K
Faculty of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Tokushima 770-8585, Japan.
Ikee
Yoshifumi
Y
Goto
Satoru
S
Shiro
Motoo
M
Nagao
Yoshimitsu
Y
D001372:Aza Compounds / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D003500:Cyclization; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry; D011437:Propylamines / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
C488447:1-azabicyclo(1,1,0)butane; C488446:2,3-dibromopropylamine hydrobromide; D001372:Aza Compounds; D001643:Bridged Bicyclo Compounds; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D011437:Propylamines; C434823:n-butyllithium