4114-99-2Relevant articles and documents
Isomerization of Cyclooctene and Cyclododecene Oxides Catalyzed by Solid Acids and Bases
Arata, Kazushi,Nakamura, Hideo,Nakamura, Yuki
, p. 2351 - 2353 (2007/10/02)
The title reactions were carried out over seven catalysts.From cyclooctene oxide a large amount of 7-octenal was formed together with 3-cycloocten-1-ol over SiO2-Al2O3 and SiO2-TiO2, 3-cycloocten-1-ol over solid H3PO4, and cyclooctanone over FeSO4.Most catalysts except for NiSO4, Al2O3, and Tio2-ZrO2 produced 1,3-cyclododecadiene, cyclododecanone, and 2-cyclododecen-1-ol uniformly from cyclododecene oxide.Allylic alcohols were preferentially given by Al2O3 and TiO2-ZrO2.
Displacement Stereochemistry and Product-Formation Selectivities in the Solvolysis of Cyclooctyl p-Bromobenzenesulfonate
Nordlander, J. Eric,Owuor, Philip O.,Cabral, Donna J.,Haky, Jerome E.
, p. 201 - 206 (2007/10/02)
Configurational analysis by 2H NMR of the products of solvolysis of (E)-cyclooctyl-2-d and (E)-cyclooctyl-4-d brosylate in acetic acid and 80percent acetone has established that substitution without rearrangement occurs with complete retention of configuration while substitution under 1,5-hydride shift takes place with complete inversion at the migration origin.The reaction is concluded to proceed by direct initial formation of a 1,5-hydrogen-bridged cation.Solvolysis of cyclooctyl-1-d brosylate in several solvents has shown elimination to be favored from C-1 over the C-5 side, whereas selectivities for competitive substitutions are similar at the two positions.Elimination is thus indicated to take place largely from first-formed tight ion pairs while displacement proceeds through more dissociated intermediates.
Oxymetallation. Part 13. Synthesis of Bicyclic Peroxides via Peroxymercuriation of Cyclic Dienes
Bloodworth, A.J.,Khan, Jamil A.,Loveitt, M.E.
, p. 621 - 632 (2007/10/02)
The bis-mercuriated derivative (12) of 9,10-dioxabicyclodecane has been prepared by peroxymercuriation of cis,cis-octa-1,5-diene, but substantial amounts of bicyclic ethers are also formed in the reaction.The bicyclic peroxides (4) and (5) have been obtained from (12) by reduction and brominolysis respectively. 8,9-Dioxabicyclodecane (6) and the dibromo-derivative (7) have similarly been prepared by peroxymercuriation and demercuriation of cyclo-octa-1,4-diene.It is suggested that the isomeric purity of the peroxides and the concurrent formation of bicyclic ethers both result from equilibrium control of reversible (per)oxymercuriation-de(per)oxymercuriation.A low yield of the -peroxide (8) has been obtained by peroxymercuriation and brominolysis of cyclohexa-1,4-diene, but attempts to prepare -compounds from 5,5-disubstituted cyclopentadienes have been unsuccessful.