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Pure Appl. Chem., 1980, Vol. 52, No. 12, pp. 2669-2682

http://dx.doi.org/10.1351/pac198052122669

The inter- and intramolecular photocycloaddition of ethylenes to aromatic compounds

Andrew Gilbert

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  • Cyclopentanoide Naturstoffe durch Alken-Addition an Aromaten. Nachr Chem Tech Lab 2010, 31, 262. <http://dx.doi.org/10.1002/nadc.19830310406>
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  • Osselton E. M., Lempers E. L. M., Eyken C. P., Cornelisse J.: Substituent effects on the meta photocycloaddition of arenes to alkenes. Recl Trav Chim Pays-Bas 2010, 105, 171. <http://dx.doi.org/10.1002/recl.19861050602>
  • Osselton E. M., Krijnen E. S., Lempers E. L. M., Cornelisse J.: The meta photocycloaddition of fluoroarenes to cyclopentene. Recl Trav Chim Pays-Bas 2010, 105, 375. <http://dx.doi.org/10.1002/recl.19861051010>
  • de Vaal P., Osselton E.M., Krijnen E.S., Lodder G., Cornelisse J.: The meta photocycloaddition of alkyl- and alkoxy-substituted arenes to cyclopentene. Recl Trav Chim Pays-Bas 2010, 107, 407. <http://dx.doi.org/10.1002/recl.19881070603>
  • Chappell David, Russell Andrew T.: From ?-cedrene to crinipellin B and onward: 25 years of the alkene?arene meta-photocycloaddition reaction in natural product synthesis. Org Biomol Chem 2006, 4, 4409. <http://dx.doi.org/10.1039/b614011b>
  • Boyd Joseph W., Greaves Nicola, Kettle Jason, Russell Andrew T., Steed Jonathan W.: Alkene-Arenemeta Photocycloadditions with a Four-Carbon-Atom Tether: Efficient Approach toward the Polycyclic Ring Systems of Aphidicolin and Stemodinone. Angew Chem 2005, 117, 966. <http://dx.doi.org/10.1002/ange.200461661>
  • Boyd Joseph W., Greaves Nicola, Kettle Jason, Russell Andrew T., Steed Jonathan W.: Alkene-Arenemeta Photocycloadditions with a Four-Carbon-Atom Tether: Efficient Approach toward the Polycyclic Ring Systems of Aphidicolin and Stemodinone. Angew Chem Int Ed 2005, 44, 944. <http://dx.doi.org/10.1002/anie.200461661>
  • Piet Dennis, De Bruijn Serge, Sum Jane, Lodder Gerrit: New molecular entities via intermolecular meta photocycloaddition. J Heterocyclic Chem 2005, 42, 227. <http://dx.doi.org/10.1002/jhet.5570420208>
  • Desmet Koen, Sandra Pat, Vízvárdi Kristóf, Hoornaert Georges J., Van der Eycken Erik: Enantioselective packed column SFC for the separation of 2-oxatetracyclo [5.4.0.01,8.05,11] undec-9-ene derivatives. J Micro Sep 2001, 13, 163. <http://dx.doi.org/10.1002/mcs.1036>
  • Barentsen Helma M., Sieval Alex B., Cornelisse Jan: Intramolecular meta photocycloaddition of conformationally restrained 5-phenylpent-1-enes. Part II: Steric and electronic effects caused by 4-mono- and 4-disubstitution. Tetrahedron 1995, 51, 7495. <http://dx.doi.org/10.1016/0040-4020(95)00374-H>
  • de Zwart E.W., de Haan R., Cornelisse J.: Intramolecular meta photocycloaddition of vinyl ethers to the benzene ring. J Photochem Photobiol A Chem 1994, 77, 161. <http://dx.doi.org/10.1016/1010-6030(94)80039-1>
  • Tietze Lutz F., Beifuss Uwe: Sequentielle Transformationen in der Organischen Chemie eine Synthesestrategie mit Zukunft. Angew Chem 1993, 105, 137. <http://dx.doi.org/10.1002/ange.19931050204>
  • Ohkura Kazue, Kanazashi Nobuhiko, Okamura Kimio, Date Tadamasa, Seki Koh-ichi: A New Ring System from Photocycloaddition of 6-Chloro-1,3-dimethyluracil to p- and m-Xylene. Formation of 6-Methylene-9,11,x-trimethyl-9,11-diazapentacyclo(6.4.0.01,3.02,5.04,8)dodecane-10,12-diones. Chem Lett 1993, 667. <http://dx.doi.org/10.1246/cl.1993.667>
  • de vaal P., Lodder G., Cornelisse J.: Partial rate factors in photochemistry: Themeta photocycloaddition of methylbenzenes to cyclopentene. J Phys Org Chem 1992, 5, 581. <http://dx.doi.org/10.1002/poc.610050905>
  • Wender Paul A., Singh Sunil K.: Synthetic studies on arene-olefin cycloadditions. 11. Total synthesis of (−)-retigeranic acid. Tetrahetron Lett 1990, 31, 2517. <http://dx.doi.org/10.1016/0040-4039(90)80114-2>
  • Neijenesch H.A., Ridderikhoff E.J., Ramsteijn C.A., Cornelisse J.: Intramolecular meta photocycloaddition of 6-arylhex-2-enes. J Photochem Photobiol A Chem 1989, 48, 317. <http://dx.doi.org/10.1016/1010-6030(89)87013-3>
  • Fenton Gary A., Gilbert Andrew: Tricyclo[3.3.0.028]oct-3-enes: Their acid cleavage reactions and cycloadditions with dienophiles. Tetrahedron 1989, 45, 2979. <http://dx.doi.org/10.1016/S0040-4020(01)80125-3>
  • Cano-Yelo Herminia, Deronzier Alain, Schuster David I., Wilczak Wojciech A., De Chang Susan Piotti, Brown Pamela B., Levi Alberto, Mattay Jochen, Runsink Jan, Hertel Regina, Kalbe Jochen, Schewe Irmgard: Photocatalysis of the pschorr reaction by Ru(bpy)32+. Journal of Photochemistry 1987, 37, 315. <http://dx.doi.org/10.1016/0047-2670(87)85013-X>
  • Mattay Jochen, Sivaram B.M., Ramalingam A., Govindanunny T., Palanisamy P.K., F��rgeteg S., B��rces T.: Selectivities in photocycloadditions of arenes to olefins. Journal of Photochemistry 1987, 37, 167. <http://dx.doi.org/10.1016/0047-2670(87)85038-4>
  • Van Der Hart J.A., Mulder J.J.C., Cornelisse J., Murthy V.R., Kumar R.Jeevan, Bouchoux G.: The meta photocycloaddition of benzene to ethylene semi-empirical calculations. Journal of Molecular Structure: THEOCHEM 1987, 151, 1. <http://dx.doi.org/10.1016/0166-1280(87)85038-8>
  • Mattay Jochen, Runsink Jan, Gersdorf Joachim, Rumbach Thomas, Ly Cuong: Selectivity and Charge Transfer in Photoreactions of α,α,α-Trifluorotoluene with Olefins. HCA 1986, 69, 442. <http://dx.doi.org/10.1002/hlca.19860690226>
  • S̆ket Boris, Zupanc̆ic̆ Natas̆a, Zupan Marko: Evidence for intramolecular [2+2] cycloaddition process in the photo-claisen rearrangement. Tetrahedron 1986, 42, 753. <http://dx.doi.org/10.1016/S0040-4020(01)87481-0>
  • Bryce-Smith D., Gilbert A., Mattay J.: Factors influencing the relative tendencies for and cycloadditions of ethylenic compounds to the benzene ring. Tetrahedron 1986, 42, 6011. <http://dx.doi.org/10.1016/S0040-4020(01)96085-5>
  • Jans A. W. H., Van Arkel B., Osselton E. M., Cornelisse J.: Proton NMR study of methyl- and fluoro-substituted 6- and 7-ethoxy-1-methoxytricyclo[3.3.0.02,8]oct-3-enes. Magn Reson Chem 1985, 23, 540. <http://dx.doi.org/10.1002/mrc.1260230712>
  • Osselton E.M., Cornelisse J., Mattay J.: The meta photocycloaddition of anisole and benzene to 2-methyl-1,3-dioxole. Journal of Photochemistry 1985, 31, 381. <http://dx.doi.org/10.1016/0047-2670(85)85105-4>
  • Mattay Jochen: Selectivity and charge transfer in photoreactions of arenes with olefins. Tetrahedron 1985, 41, 2405. <http://dx.doi.org/10.1016/S0040-4020(01)96636-0>
  • Osselton E.M., Cornelisse J.: The meta photocycloaddition of benzonitrile and α,α,α-trifluorotoluene to cyclopentene. Tetrahetron Lett 1985, 26, 527. <http://dx.doi.org/10.1016/S0040-4039(00)61929-9>
  • Drew Michael G.B., Gilbert Andrew, Rodwell Paul W.: Photoaddition reactions of dichloroethylene with benzenoid compounds: facile formation of tetracyclo[3.3.0.02,804,6]octanes and semibullvalenes. Tetrahetron Lett 1985, 26, 949. <http://dx.doi.org/10.1016/S0040-4039(00)61972-X>
  • Osselton E.M., Eyken C.P., Jans A.W.H., Cornelisse J.: The meta photocycloaddition of anisole and benzonitrile to 1,3-dioxol-2-one. Tetrahetron Lett 1985, 26, 1577. <http://dx.doi.org/10.1016/S0040-4039(00)98556-3>
  • de Vaal P., Lodder G., Cornelisse J.: Deuterium isotope effects in the meta photocycloaddition of aromatic compounds to alkenes. Tetrahetron Lett 1985, 26, 4395. <http://dx.doi.org/10.1016/S0040-4039(00)98745-8>
  • Ellis-Davies G.C.R., Gilbert A., Warrington J.V., Westover D.L.: Photochemical reactions of phenyl-dienyl non- conjugated bichromophoric systems. Journal of Photochemistry 1984, 27, 259. <http://dx.doi.org/10.1016/0047-2670(84)85043-1>
  • Jans A.W.H., van Arkel B., van Dijk-Knepper J.J., Mioch H., Cornelisse J.: The meta photocycloaddition of anisole to oxa- and dioxa-cyclopentenes and to ethyl vinyl ether. Tetrahedron 1984, 40, 5071. <http://dx.doi.org/10.1016/S0040-4020(01)91256-6>
  • Kashoulis Annoula, Gilbert Andrew, Ellis-Davies Graham: Photochemical reactions of naphthyl-vinyl non-conjugated bichromophoric systems. Tetrahetron Lett 1984, 25, 2905. <http://dx.doi.org/10.1016/S0040-4039(01)81322-8>
  • Gilbert Andrew, Yianni Paul: Mechanisms and selectivities in the photocycloaddition of ethenes to the benzene ring. Tetrahetron Lett 1982, 23, 4611. <http://dx.doi.org/10.1016/S0040-4039(00)85667-1>
  • Mattay Jochen, Runsink Jan, Leismann Hans, Scharf Hans-Dieter: Photochemical cycloaddition of olefie to aromatic compounds -IV. on the mechanism of the photochemical meta-cycloaddition. Tetrahetron Lett 1982, 23, 4919. <http://dx.doi.org/10.1016/S0040-4039(00)85747-0>
  • Gilbert Andrew, Yianni Paul: Solvent polarity effects on the regioselectivity of photoaddition reactions of arene-ethene systems. Tetrahetron Lett 1982, 23, 255. <http://dx.doi.org/10.1016/S0040-4039(00)86801-X>
  • Sheridan Robert S.: A reinvestigation of the meta—photoadditions of cyclooctene to anisole and toluene. Tetrahetron Lett 1982, 23, 267. <http://dx.doi.org/10.1016/S0040-4039(00)86805-7>
  • Bryce-Smith D., Fenton G.A., Gilbert A.: Mechanism of the photochemical -cycloaddition of alknes to the benzene ring. Tetrahetron Lett 1982, 23, 2697. <http://dx.doi.org/10.1016/S0040-4039(00)87435-3>
  • Gilbert A., Krestonosich S., Wilson S.: Excited state reactions of arene-ethene-amine trichromophoric systems. Tetrahetron Lett 1982, 23, 4061. <http://dx.doi.org/10.1016/S0040-4039(00)88696-7>
  • Gilbert Andrew, Yianni Paul: Regio- and stereo-selectivities of the ortho and meta photocycloaddition reactions of ethylenes to benzene and its simple derivatives. Tetrahedron 1981, 37, 3275. <http://dx.doi.org/10.1016/S0040-4020(01)92375-0>