title: Trisequential photooxygenation reaction: application to the synthesis of carbasugars.
abstract: 4,5-Dimethylenecyclohex-1-ene was subjected to a photooxygenation reaction to introduce oxygen functionalities. The endoperoxide obtained underwent an ene-reaction to form hydroperoxides with 1,3-diene structures. Further addition of singlet oxygen to the diene units resulted in the formation of tricyclic hydroperoxides having three oxygens in the molecule. Cleavage of the oxygen-oxygen bonds followed by epoxidation of the remaining C-C double bond and concomitant ring-opening reaction furnished the isomeric carbasugars.
authors: Department of Chemistry, Sakarya University, 54100 Sakarya, Turkey. abaran@sakarya.edu.tr
authors: Arif
authors: A
authors: Baran
authors: Gokay
authors: G
authors: Aydin
authors: Tahir
authors: T
authors: Savran
authors: Ertan
authors: E
authors: Sahin
authors: Metin
authors: M
authors: Balci
mesh_terms: D054329:Carbasugars / Q000138:chemical synthesis* / Q000737:chemistry; D053138:Cyclohexenes / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D026082:Singlet Oxygen / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C586179:4,5-dimethylenecyclohex-1-ene; D054329:Carbasugars; D053138:Cyclohexenes; D026082:Singlet Oxygen; D006861:Hydrogen Peroxide