Journal article

Publication year: 2011

Pages: 1695-1702

Journal: Russian Journal of Organic Chemistry

Volume number: 47

Issue number: 11

ISSN: 1070-4280

DOI Link: https://doi.org/10.1134/S1070428011110078

Publisher: Springer

Abstract: 
The mixture of di- and monoethylene ketals obtained by the reaction of 1,9-dibromopentacyc lo[5.4.0.0(2,6).0(3,10).0(5,9)]-undeca-8,11-dione followed by hydrolysis and ring contraction by Faworsky method was converted into a mixture of ethylene ketals of 7-bromopentacyclo[5.3.0.0(2,5).0(3,9).0(4,8)]decan-6-one-4- and 5-bromopentacyclo[5.3.0.0(2,5).0(3,9).0(4,8)]decan-6-one-8-carboxylic acid where the carboxy group was replaced by bromine along the procedure of Hunsdiecker-Borodine-Cristol. 6-Ethylene ketal of the pentacyclo[5.3.0.0(2,5).0(3,9).0(4,8)] decan-6-one obtained by the debromination of ethylene ketals of 4,7- and 5,8-dibromopentacyclo[5.3.0.0(2,5).0(3,9).0(4,8)] decan-6-one was hydrolyzed to ketone whose oxime was selectively reduced on a platinum catalyst into the di-6-pentacyclo[5.3.0.0(2,5).0(3,9).0(4,8)]decylamine. The reaction of reductive dimerization was also characteristic of pentacyclo[4.3.0.0(2,5).0(3,8).0(4,7)]-nonan-9-one and pentacyclo[6.3.0.0(2,6).0(3,10).0(5,9)]undecan-4-one oximes, whereas the composition of the reduction products of pentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecan-8-one oxime depended on the amount of the catalyst.

Harvard Citation style: Rodionov, V., Sklyarova, A., Shamota, T., Schreiner, P. and Fokin AA (2011) Selective reductive dimerization of homocubane series oximes, Russian Journal of Organic Chemistry, 47(11), pp. 1695-1702. https://doi.org/10.1134/S1070428011110078

APA Citation style: Rodionov, V., Sklyarova, A., Shamota, T., Schreiner, P., & Fokin AA (2011). Selective reductive dimerization of homocubane series oximes. Russian Journal of Organic Chemistry. 47(11), 1695-1702. https://doi.org/10.1134/S1070428011110078