52148-56-8Relevant academic research and scientific papers
Photocatalytic Properties of a Palladium Metallosquare with Encapsulated Fullerenes via Singlet Oxygen Generation
Martínez-Agramunt, Víctor,Peris, Eduardo
supporting information, p. 11836 - 11842 (2019/09/03)
Singlet oxygen has recently attracted a great deal of attention due to its strong oxidizing properties, which makes it useful in organic synthesis and biological studies. However, the photosensitizers that are required for singlet oxygen generation remain
Continuous Endoperoxidation of Conjugated Dienes and Subsequent Rearrangements Leading to C-H Oxidized Synthons
De Souza, Juliana M.,Brocksom, Timothy J.,McQuade, D.Tyler,De Oliveira, Kleber T.
, p. 7574 - 7585 (2018/06/11)
We have investigated the continuous flow photooxidation of several conjugated dienes and subsequent rearrangement using a practical and safe continuous-flow homemade engineered setup. End-to-end approaches involving endoperoxidation, Kornblum-DeLaMare rearrangement, and additional rearrangements are comprehensively detailed with optimization, scope, and scale-up to obtain useful hydroxyenones, furans, and 1,4-dicarbonyl building blocks.
Concise entry to chiral 5-(4-Hydroxybutyl)-2(5 H)-furanone via HTIB-mediated novel oxidative fragmentation: Formal total synthesis of (+)-dubiusamine A
Kawasumi, Muneo,Iwabuchi, Yoshiharu
supporting information, p. 1788 - 1790 (2013/06/26)
The concise synthesis of 5-(4-hydroxybutyl)-2(5H)furanone has been accomplished from 9-oxabicyclo[4.2.1]non-7-en-1-ol on the basis of HTIB [PhI(OH)OTs, a.k.a. Koser's reagent]-mediated novel oxidative fragmentation. Chiral (-)-(R)-5-(4-hydroxy-butyl)-2(5H
A concise and stereospecific synthesis of some cyclitols containing eight-membered rings: cyclooctane-1,2,3,4-tetraoles
Salamci, Emine
experimental part, p. 4010 - 4015 (2010/07/06)
A concise and efficient synthesis of cyclooctane-1,2,3,4-tetraoles, new polyhydroxylated eight-membered carbocycles, is described starting from cis,cis-1,3-cyclooctadiene. Cyclooctene endoperoxide obtained by photooxygenation of cis,cis-1,3-cyclooctadiene was the key compound in the synthesis. Reduction of the endoperoxide with zinc or thiourea followed by acetylation of the hydroxyl group and OsO4/NMO oxidation of the double bond gave (1R(S),2S(R),3R(S),4S(R))-cyclooctane-1,2,3,4-tetraol. Interestingly, epoxidation of cyclooctene-1,4-diol with m-CPBA also afforded trans-epoxy-diol 17. (1R(S),2R(S),3R(S),4S(R))-cyclooctane-1,2,3,4-tetraol was easily obtained by hydrolysis of epoxy-diol 17.
Palladium-catalyzed cyclopropanation of unsaturated endoperoxides. A new peroxide-preserving reaction
Emerzian, Michael A.,Davenport, William,Song, Jiangao,Li, Jim,Erden, Ihsan
experimental part, p. 999 - 1004 (2009/12/06)
Unsaturated bicyclic endoperoxides are efficiently cyclopropanated with excess diazomethane in the presence of catalytic palladium(II) acetate [Pd(OAc)2] in a stereoselective manner. This method represents a new peroxide-preserving transformati
A seco-porphyrazine: Superb sensitizer for singlet oxygen generation and endoperoxide synthesis
Trabanco, Andrés A.,Montalban, Antonio Garrido,Rumbles, Garry,Barrett, Anthony G. M.,Hoffman, Brian M.
, p. 1010 - 1012 (2007/10/03)
seco-Porphyrazine 2 was found to effectively catalyze the [4+2] cycloaddition of singlet oxygen to a range of 1,3-dienes under mild conditions.
Synthesis and Tautomerism of 9-Azabicyclononan-1-ols (Norhomotropan-1-ols), N-Alkyl and 7,8-Dehydro-Derivatives, and Oxabicyclic Analogues
Smith, Craig R.,Justice, David E.,Malpass, John R.
, p. 11039 - 11056 (2007/10/02)
9-Methyl-9-azabicyclononan-1-ol (homotropan-1-ol; homophysoperuvine) and -non-7-en-1-ol (homotrop-7-en-1-ol) have been synthesized together with the nor- systems and N-benzyl derivatives.The bicyclic amino-alcohols are shown to be in tautomeric equ
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.
