86359-56-0Relevant academic research and scientific papers
ADDITION OF HYDROGEN BROMIDE TO CIS-BICYCLONONA-3,7-DIENE. SYNTHESIS OF 5-BROMOBREXANE AND BREXAN-5-ONE
Dubitskaya, N. F.,Khaibullina, E. A.,Pekhk, T. I.,Grishin, Yu. K.,Belikova, N. A.,Bobyleva, A. A.
, p. 1589 - 1593 (2007/10/02)
The addition of hydrogen bromide to cis-bicyclonona-3,7-diene takes place preferentially but not selectively at the double bond of the six-membered ring.In the case of gaseous hydrogen bromide only bromobicyclononenes are formed, but with 48percent aqueous hydrobromic acid the reaction is accompanied by transannular cyclization and by the formation of endo- and exo-5-bromobrexanes (16-20percent).A method is proposed for the production of brexan-5-one.
TRANSANNULAR CYCLIZATION OF 3-METHYL-cis-BICYCLONONA-2,7-DIENE AND 3-METHYL- AND 3,4-DIMETHYL-cis-BICYCLONONA-3,7-DIENES. SYNTHESIS OF 5-SUBSTITUTED BREXANES
Anfilogova, S. N.,Nigmatova, V. B.,Pekhk, T. I.,Belikova, N. A.,Koptev, D. A.
, p. 1708 - 1713 (2007/10/02)
The reaction of formic acid and acetic acid with 3-methyl-cis-bicyclonona-2,7-diene, 3-methyl- and 3,4-dimethyl-cis-bicyclonona-3,7-dienes, and 3-methyl-cis-bicyclonon-7-en-3-ol leads to the exclusive formation of esters of 1-methyl- or 1,9-dimethyl-exo-brexan-5-ol with yields of 80-90percent.The reaction can be used as a convenient preparative method for the synthesis of 5-substituted brexanes.
HYDROBORATION AND OXYMERCURATION-DEMERCURATION OF CIS-BICYCLONONA-3,7-DIENE. SYNTHESIS OF CIS-BICYCLONONENONES
Arbuzov, V. A.,Pekhk, T. I.,Belikova, N. A.,Bobyleva, A. A.,Plate, A. F.
, p. 273 - 282 (2007/10/02)
Four isomeric cis-bicyclononenones were obtained from cis-bicyclonona-3,7-diene by hydroboration and oxymercuration-demercuration.Their structures were determined by means of their 13C NMR spectra.The addition of the hydroborating agents takes place preferentially (60-80percent) at the cyclopentene double bond at the C7 and C8 atoms and is most selective in the case of 9-borabicyclononane.The direction of addition of mercuric acetate depends on the solvent; the reaction takes place most selectively (95percent) at the cyclohexene double bond in 1:9 aqueous THF, and here the mercury adds to the C4 carbon atom to the extent of 90percent.
