title: Photoinduced reactions of bicycloalkylidenes with isatin and isoquinolinetrione.
abstract: Photoinduced reactions of isatin and N-methyl-1,3,4-isoquinolinetrione with bicycloalkylidenes such as bicyclopropylidene, cyclopropylidenecyclobutane, cyclopropylidenecyclohexane and bicyclohexylidene were investigated. The reactions gave spirooxetanes as the major products derived from the [2 + 2] photocycloaddition pathway via 1,4-biradical recombination. Unusual products including the [4 + 2 + 2] cycloadducts, the oxoisochroman derivatives and other ring-rearranged products were derived from competitive pathways via 1,6-biradical recombination. The presence of oxygen in the reaction solution was found to be relevant to the distribution of different types of products. Mechanisms were proposed to rationalize the chemo- and regioselectivity in the photoreactions and the origin of the different types of products.
authors.affiliation: School of Chemistry and Chemical Engineering, State Key Laboratory of Analytical Chemistry for Life Science, Nanjing University, Nanjing, PR China.
authors.forename: Dong-Dong
authors.initials: DD
authors.lastname: Wu
authors.forename: Ming-Tao
authors.initials: MT
authors.lastname: He
authors.forename: Qi-Di
authors.initials: QD
authors.lastname: Liu
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.forename: Jie
authors.initials: J
authors.lastname: Zhou
authors.forename: Lei
authors.initials: L
authors.lastname: Wang
authors.forename: Hoong-Kun
authors.initials: HK
authors.lastname: Fun
authors.forename: Jian-Hua
authors.initials: JH
authors.lastname: Xu
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhang
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D007546:Isoquinolines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D055668:Photochemical Processes; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D001643:Bridged Bicyclo Compounds; D004988:Ethers, Cyclic; D007546:Isoquinolines; D013141:Spiro Compounds; D007510:Isatin; C005287:oxetane