53921-54-3Relevant academic research and scientific papers
ISOMERIC CIS-BICYCLONONADIENES
Gevorkyan, G. G.,Belikova, N. A.,Bobyleva, A. A.,Pekhk, T. I.,Anfilogova, S. N.,et al.
, p. 1583 - 1588 (2007/10/02)
cis-Bicyclonona-2,7-dienes and the corresponding 2,8-dienes were obtained by the isomerization of cis-bicyclonona-3,7-diene and dehydration of the cis-bicyclonon-7(8)-en-3-ols.The 13C and PMR spectra of the isomeric dienes were investigated, and their retention times in GLC analysis were determined.The reaction of cis-bicyclonona-3,7-diene with N-bromosuccinimide in aqueous DMSO and the reaction of cis-bicyclonona-2,7-diene with acetic acid were studied.
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.
ADDITION OF ORGANIC ACIDS TO cis-BICYCLONONA-3,7-DIENE. SYNTHESIS OF COMPOUNDS OF THE BREXANE AND BRENDANE SERIES
Arbuzov, V. A.,Gevorkyan, G. G.,Pekhk, T. I.,Bobyleva, N. A.,Belikova, N. A.
, p. 1114 - 1124 (2007/10/02)
The esters of cis-bicyclononenols, exo- and endo-brexan-5-ols, and exo-brendan-2-ol were obtained by the addition of formic, acetic, and trifluoroacetic acids to cis-bicyclonona-3,7-diene.The composition of the reaction products and its dependence on the reaction conditions were determined.A method is proposed for the separation of the bicyclic and tricyclic components.The mechanism of the transannular cyclization is discussed.
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.
