Sciact
  • EN
  • RU

Synthesis of nine-, ten-, and fifteen-membered alkenolides by the oxidative cleavage of the bridging C=C bond in 2-oxabicycloalkenes Full article

Journal Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285
Output data Year: 2001, Volume: 50, Number: 11, Pages: 2149-2155 Pages count : 7 DOI: 10.1023/a:1015009603719
Authors Ogibin Yu.N. 1 , Terent"ev A.O. 1 , Ananikov V.P. 1 , Nikishin G.I. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

Abstract: Hydroperoxidation of C=C-bridged 2-oxabicycloalkenes in which the five- or six-membered oxacycle is fused with the five-, six-, or twelve-membered hydrocarbon ring was studied. The Cu(OAc)2-catalyzed decomposition of the resulting hydroperoxides afforded nine-, ten-, or fifteen-membered trans-alkenolides, respectively. The latter compounds were obtained as pairs of regioisomers, with the isomers in which the double bond is more remote from the ether oxygen atom predominating.
Cite: Ogibin Y.N. , Terent"ev A.O. , Ananikov V.P. , Nikishin G.I.
Synthesis of nine-, ten-, and fifteen-membered alkenolides by the oxidative cleavage of the bridging C=C bond in 2-oxabicycloalkenes
Russian Chemical Bulletin. 2001. V.50. N11. P.2149-2155. DOI: 10.1023/a:1015009603719 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000175056400030
Scopus: 2-s2.0-0035647952
OpenAlex: W2950549608
Citing:
DB Citing
OpenAlex 13
Scopus 11
Web of science 14
Altmetrics: