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Communication | Special issue | Vol 30, No. 1, 1990, pp.237-240
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S13
Synthesis of Novel Carbo- and Heteropolycycles. 17. Intramolecular 1,3-Dipolar Cycloaddition Reaction of 3-endo-Azidobicyclo[3.3.1]non-6-ene. A Facile Route to 5-Azaprotoadamant-4-ene

Shoji Eguchi,* Takanori Suzuki, Nao Toi, and Tadashi Sasaki

*Faculty of Engineering, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan


The intramolecular 1,3-dipolar cycloaddition of 3-endo-azidobicyclo[3.3.1]non-6-ene 1 proceeded on heating in toluene under reflux to afford regioselectively very unstable 1,2,3-triazoline derivative 2, which decomposed spontaneously in MeOH to give exclusively 5-azaprotoadamant-4-ene 6.