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Mechanistic Considerations for the Consecutive Cyclization of 2,3-Dibromopropylamine Hydrobromide Giving a Strained Molecule, 1-Azabicyclo[1.1.0]butane
2004 年 52 巻 1 号 p. 89-94
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2004 年 52 巻 1 号 p. 89-94
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.
