6319-15-9Relevant academic research and scientific papers
Synthesis of certain unsubstituted, 9-exo-(dialkylaminomethyl)-, and 9- endo-(aralkyl)-tricyclo [5.2.1.02,6 decane-8-ketoxime esters and ethers with local anesthetic and analgesic activities
Aboul-Enein M, Nabil,El-Azzouny, Aida,Abdallah, Nevine A.,Maklad, Yousreya A.,Saleh, Ola A.,Ebeid
, p. 197 - 208 (2007/10/03)
The synthesis of series of unsubstituted, 9-exo-(dialkylaminomethyl)-, and 9-endo-(aralkyl)tricyclo [5.2.1.0(2,6)] decane-8-ketoximes esters and ethers 3a-j, 4a-d, 7a-j and 13a-d from the oxime synthons 2, 6a-e, 12a and 12b, respectively, is described. Al
BECKMANN REACTION OF FRAMEWORK SUBSTRATES. III. REACTION OF KETONES OF THE TRICYCLO2,6>DECANE SERIES WITH HYDROXYLAMINE-O-SULFONIC ACID IN ORGANIC AND AQUEOUS ORGANIC SOLVENTS
Klimko, Yu. E.,Isaev, S. D.,Yurchenko, A. G.,Chernyaev, B. V.
, p. 877 - 883 (2007/10/02)
The possibility of the preparative realization of the Beckmann reaction with hydroxylamine-O-sulfonic acid in a homogeneous medium was demonstrated for the case of tricyclo2,6>dec-3-en-9-one and tricyclo2,6>dec-4-en-9-one.The intermediate reaction products (oxime sulfates) were isolated in the form of the ammonium salts.They are converted into the same lactams and bicyclic unsaturated hydroxynitriles as the ketones in the direct reaction.In acetonitrile the corresponding acetaminonitriles are formed instead of the hydroxynitriles.In anhydrousorganic solvents or with a small content of water the direction of the process changes toward the preferential formation of the oximes.The nature of the dependence of the solvolysis rate on the acceptor and donor numbers of tetrahydrofuran, dioxane, acetone, dimethylformamide, and dimethyl sulfoxide confirms the carbenium-ion mechanism of the process.
