53646-92-7Relevant academic research and scientific papers
Electron-transfer Photochemistry of Endoperoxides
Takahashi, Yasutake,Wakamatsu, Kan,Morishima, Shin-ichi,Miyashi, Tsutomu
, p. 243 - 253 (1993)
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.
Dihydroxylation of 4-substituted 1,2-dioxines: A concise route to branched erythro sugars
Robinson, Tony V.,Pedersen, Daniel Sejer,Taylor, Dennis K.,Tiekink, Edward R. T.
supporting information; experimental part, p. 5093 - 5096 (2009/10/17)
(Chemical Equation Presented) The synthesis of 2-C-branched erythritol derivatives, including the plant sugar (±)-2-C-methylerythritol 2, was achieved through a dihydroxylation/reduction sequence on a series of 4-substituted 1,2-dioxines 3. The asymmetric dihydroxylation of 1,2-dioxines was examined, providing access to optically enriched dihydroxy 1,2-dioxanes 4. The synthesized 1,2-dioxanes were converted to other erythro sugar analogues and tetrahydrofurans through controlled cleavage of the endoperoxide linkage.
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.
