Journal of the Chemical Society. Perkin transactions I p. 2529 - 2534 (1983)
Update date:2022-08-11
Topics:
Sasaki, Tadashi
Eguchi, Shoji
Toi, Nao
Okano, Takashi
Furukawa, Yoshio
The acidolysis of 3-endo-azidomethylbicyclo<3.3.1>non-6-ene (3) with methanesulphonic acid gave 4-azahomoadamant-4-ene (5) which was also produced from 3-endo-hydroxymethylbicyclo<3.3.1>non-6-ene (6) on treatment with NaN3-MeSO3H.The formation of (5) was rationalized by a ? route cyclization followed by acidolytic ring expansion of intermediate azides on the basis of acidolysis of dideuterio- derivatives.The above route was extended to synthesis of 2,2- (16) and 7,7-dimethyl-4-azahomoadamant-4-enes (17).The acidolysis of 3-endo-azidobicyclo<3.3.1>non-6-ene (23) gave 2 -aza-adamantan-anti-4-ol (26) via a ?-N+ type cyclization.
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