81238-63-3Relevant academic research and scientific papers
Electron-transfer Photochemistry of Endoperoxides
Takahashi, Yasutake,Wakamatsu, Kan,Morishima, Shin-ichi,Miyashi, Tsutomu
, p. 243 - 253 (2007/10/02)
Derivatives of 1,2-dioxacyclohex-4-ene and 2,3-dioxabicyclooct-5-ene (endoperoxides, EPs) form EDA complexes with tetracyanoethylene (TCNE).The phenyl-substituted EPs 3a, 4a, 4b and 6 undergo electron-transfer-induced reactions when the EDA complexes are irradiated.Two types of reactions are observed depending on the ring system.Monocyclic EPs (3a, 4a and 4b) afford furan derivatives, possibly through the Criegee-type rearrangement, and dehydration, whereas the bicyclic EP 6 undergoes cycloreversion through the C-O bond cleavage.
PALLADIUM(0) CATALYZED REACTIONS OF 1,4-EPIPEROXIDES
Suzuki, Masaaki,Oda, Yoshihisa,Hamanaka, Nobuyuki,Noyori, Ryoji
, p. 517 - 535 (2007/10/02)
The Pd(PPh3)4 catalyzed reaction of 2,3-saturated and 2,3-unsaturated 1,4-epiperoxides proceeds by courses markedly different from those of the previously reported transition metal catalyses.The Pd(0)-promoted reaction of 2,3-saturated epiperoxides gives the corresponding 4-hydroxy ketones and 1,4-diols as the major products.From 2,3-dedihydroepiperoxides are formed the corresponding 4-hydroxy enones, syn-1,2;3,4-diepoxides, and 1,4-diols.The results are interpreted in terms of competing Pd(0)/Pd(II) exchange mechanisms.Exposure of prostaglandin (PG) H2 methyl esterto Pd(PPh3)4 produces a mixture of methyl esters of PGD2, PGE2, PGF2α, and (5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid.
SENSITIZED PHOTO-OXYGENATION OF ACYCLIC CONJUGATED DIENES
Matsumoto, Masakatsu,Dobashi, Satoshi,Kuroda, Keiko,Kondo, Kiyosi
, p. 2147 - 2154 (2007/10/02)
Sensitized photo-oxygenation of a wide variety of acyclic 1,3-dienes was investigated.The 1,4-cycloaddition of singlet oxygen to acyclic conjugated dienes was closely related to the thermal Diels-Alder reaction in stereospecificity, and steric and electronic effects of substituents.Reactivity order of singlet oxygen toward conjugated dienes and isolated C-C double bonds was exhibited as follows: trisubstituted monoolefins > 2-substituted 1,3-dienes > disubstituted mono-olefins.
