title: Investigating the arenyl-diene double [3 + 2] photocycloaddition reaction.
abstract: The double [3 + 2] photocycloaddition reaction involving arenyl-dienes has been used to assemble seven separate [5.5.5.5] fenestrane structures that include ether and aza variants. The primary photolysis step was a meta photocycloaddition reaction, while a secondary photocycloaddition step formed the fenestrane structure. Investigations involving the insertion of an additional methylene group into the basic arenyl-diene skeleton failed to afford the desired [5.5.5.6] fenestrane structure. The presence of an oxime moiety in the aromatic photosubstrate allowed the primary photolysis step to take place; however, an attempted secondary photocycloaddition reaction involving the oxime did not provide the intended polyheterocyclic fenestrane. An alternative strategy to form various "criss-cross" double meta photocycloadducts was investigated and led to the discovery of a Paterno-Büchi cycloaddition reaction between acetone and an angular meta photocycloadduct. Other novel thermally and photochemically mediated skeletal rearrangement reactions were also recorded.
authors.affiliation: Department of Chemistry, University of Sussex, Brighton, BN1 9QJ, UK. Clive.Penkett@googlemail.com
authors.forename: Clive S
authors.initials: CS
authors.lastname: Penkett
authors.forename: Jason A
authors.initials: JA
authors.lastname: Woolford
authors.forename: Timothy W
authors.initials: TW
authors.lastname: Read
authors.forename: Rachel J
authors.initials: RJ
authors.lastname: Kahan
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010777:Photochemistry; D010782:Photolysis; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D001372:Aza Compounds; D004987:Ethers