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Journal articles on the topic 'Photocyclisation'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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1

Cottet, Françoise, Louis Cottier, and Gérard Descotes. "Photocyclisations de cétoacétals aromatiques en vue d'une approche synthétique de la crombénine." Canadian Journal of Chemistry 68, no. 7 (July 1, 1990): 1251–57. http://dx.doi.org/10.1139/v90-193.

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Crombenin 1 is a spiropeltogynoid compound with a spiroacetal moiety. A similar structure was synthesized starting from an orthocarbonylphenoxyisochroman by a Norrish type II photocyclisation. With an isochroman compound, the aromatic ring induces benzyl radical formation to give chiefly a bicyclic [4.3.1] derivative. However, with the introduction of electron-withdrawing or bulky substituents at C-4′, this side reaction is limited and the spiranic product becomes preponderant. Keywords: acetals, isochroman, photocyclisation, spiroacetals.

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2

Gupta, Satish C., Somesh Sharma, Mohamad Yusuf, Surinder Arora, Ashok Saini, Ramesh C. Kamboj, and Som N. Dhawan. "Photocyclisation of 3-Alkoxythiochromones: Activation for H-Abstraction." Journal of Chemical Research 2002, no. 4 (April 2002): 165–67. http://dx.doi.org/10.3184/030823402103171744.

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3

Gupta, Satish C., Mohamad Yusuf, Mandeep Thakur, and Ramesh C. Kamboj. "Photocyclisation of o-Xylylbischromones: Proximity Effect." Journal of Chemical Research 2005, no. 11 (November 2005): 741–43. http://dx.doi.org/10.3184/030823405774909469.

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The photocyclisation of thiophene and furan substituted o-xylylbischromones is described. The reaction occurs through a 1,4-biradical species. The proximity of the two chromophores due to intramolecular complex formation affects the chemical efficiency of the reaction.

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4

Klajn, Jan, Wojciech Stawski, Piotr J. Chmielewski, Joanna Cybińska, and Miłosz Pawlicki. "A route to a cyclobutane-linked double-looped system via a helical macrocycle." Chemical Communications 55, no. 31 (2019): 4558–61. http://dx.doi.org/10.1039/c9cc01201j.

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The macrocyclic confinements prefers a solid-state prearrangement of two CC linkers that after photocyclisation quantitatively form a cyclobutane linked double-looped structure with perpendicular orientation of macrocyclic arms.

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5

Mascal, Mark, and Christopher J. Moody. "Photocyclisation of haloacetyl tryptophan derivatives." Journal of the Chemical Society, Chemical Communications, no. 9 (1988): 587. http://dx.doi.org/10.1039/c39880000587.

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6

Beck, Anthony L., Mark Mascal, Christopher J. Moody, Alexandra M. Z. Slawin, David J. Williams, and William J. Coates. "Synthesis of 3,4-bridged indoles by photocyclisation reactions. Part 1. Photocyclisation of halogenoacetyl tryptophan derivatives." Journal of the Chemical Society, Perkin Transactions 1, no. 7 (1992): 797. http://dx.doi.org/10.1039/p19920000797.

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7

Müller, Matthias, Stefan Behnle, Cäcilia Maichle-Mössmer, and Holger F. Bettinger. "Boron–nitrogen substituted perylene obtained through photocyclisation." Chem. Commun. 50, no. 58 (2014): 7821–23. http://dx.doi.org/10.1039/c4cc01424c.

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A BN substituted hexabenzotriphenylene (B₃N₃) closes one C–C-bond upon irradiation in the presence of iodine to yield a phenanthrene annelated B₃N₃ tribenzoperylene. Upon hydrolysis a B₂N₂ dibenzoperylene is obtained.

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8

de Vries, Johannes G., and Sally A. Hubbard. "Conversion of benzoin into 9,10-phenanthrenequinone by photocyclisation." Journal of the Chemical Society, Chemical Communications, no. 17 (1988): 1172. http://dx.doi.org/10.1039/c39880001172.

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9

Khanna, Radhika, Aarti Dalal, Ramesh Kumar, and Ramesh C. Kamboj. "Phototransformation of 3-alkoxychromenones: regioselective photocyclisation and dealkoxylation." Photochemical & Photobiological Sciences 14, no. 12 (2015): 2195–202. http://dx.doi.org/10.1039/c5pp00318k.

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The phototransformation of some 2-(3-methoxyphenyl)-4H-chromen-4-ones bearing a propynyloxy moiety at the 3-position into 5-ethynyl-2-methoxy-6-oxa-benzo[5,6-c]xanthen-7-ones and 2-(3-methoxyphenyl)-4H-chromen-4-ones via regioselective cyclisation and dealkoxylation respectively has been described.

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10

Kessar, S. V., Tejvir Singh, and Rahul Vohra. "An interesting application of photocyclisation in aporhoeadane alkaloid synthesis." Tetrahedron Letters 28, no. 44 (January 1987): 5323–26. http://dx.doi.org/10.1016/s0040-4039(00)96720-0.

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11

Seffar, Abdessamad, Gérard Dauphin, and Pierre Boule. "Oxidative photocyclisation of 2-biphenylol in dilute aqueous solution." Chemosphere 16, no. 6 (January 1987): 1205–14. http://dx.doi.org/10.1016/0045-6535(87)90057-9.

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12

Beck, Anthony L., Mark Mascal, Christopher J. Moody, and William J. Coates. "Synthesis of 3,4-bridged indoles by photocyclisation reactions. Part 2. Photocyclisation of halogenoacetyl tryptophol derivatives and α-chloro indol-3-ylalkanoate esters." J. Chem. Soc., Perkin Trans. 1, no. 7 (1992): 813–21. http://dx.doi.org/10.1039/p19920000813.

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13

Gramain, Jean-Claude, Sylvie Mavel, Yves Troin, and Danielle Vallée-Goyet. "Photocyclisation de N-benzoylenamines. Syntheses de spirocyclohexanes en serie isoquinoleine." Tetrahedron 47, no. 35 (August 1991): 7287–300. http://dx.doi.org/10.1016/s0040-4020(01)89731-3.

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14

Fall, C. A. T., A. Diop, and J. J. Aaron. "Photocyclisation of Diphenylamine as a Fluorogenic Reaction for Photochemical-Fluorimetric Analysis." Bulletin des Sociétés Chimiques Belges 95, no. 8 (September 1, 2010): 631–40. http://dx.doi.org/10.1002/bscb.19860950806.

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15

Pardasani, R. T., P. Pardasani, S. Muktawat, R. Ghosh, and T. Mukherjee. "Photocyclisation of aroyl-1,4-quinones as precursors for anthracyclones and heteroanthracyclones." Research on Chemical Intermediates 24, no. 9 (September 1998): 973–78. http://dx.doi.org/10.1163/156856798x00663.

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16

Kavanagh, Pierce V., John M. Kelly, T. Brian H. McMurry, and John P. James. "Intramolecular photocyclisation of molecules containing both 3-phenylcyclopentenone and uracil rings." Journal of the Chemical Society, Chemical Communications, no. 3 (1993): 231. http://dx.doi.org/10.1039/c39930000231.

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17

Thiering, Swantje, Christian Sund, Joachim Thiem, Anja Giesler, and Jürgen Kopf. "Syntheses of imido-substituted glycosans and their photocyclisation towards highly functionalised heterotricycles." Carbohydrate Research 336, no. 4 (December 2001): 271–82. http://dx.doi.org/10.1016/s0008-6215(01)00250-6.

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18

Atfah, Adnan, Muhammad Y., Abu-Shuheil, and John Hill. "Photocyclisation of 2-aroylquinoxalines; formation of coloured indolo[l,2-a]quinoxalines." Tetrahedron 46, no. 18 (January 1990): 6483–500. http://dx.doi.org/10.1016/s0040-4020(01)96016-8.

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19

Bortolus, Pietro, Fausto Elisei, Giovanna Favaro, Sandra Monti, and Fausto Ortica. "Photocyclisation of 2-pyridyl phenyl ketone. A reaction driven by hydrogen bonding." Journal of the Chemical Society, Faraday Transactions 92, no. 11 (1996): 1841. http://dx.doi.org/10.1039/ft9969201841.

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20

Wonanke, A. D. Dinga, Jayne L. Ferguson, Christopher M. Fitchett, and Deborah L. Crittenden. "Predicting the Outcome of Photocyclisation Reactions: A Joint Experimental and Computational Investigation." Chemistry – An Asian Journal 14, no. 8 (February 20, 2019): 1293–303. http://dx.doi.org/10.1002/asia.201801761.

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21

Gramain, Jean-Claude, Assia Azzouzi, Moniquw Dufour, and Roland Remuson. "Photocyclisation of Keto-lactams. A New Synthesis of Functionalized 1-Azabicyclo(x.y.o)alkanes." HETEROCYCLES 27, no. 1 (1988): 133. http://dx.doi.org/10.3987/com-87-4300.

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22

Bucher, Götz, Roger Bresolí-Obach, Carme Brosa, Cristina Flors, Javier G. Luis, Teresa A. Grillo, and Santi Nonell. "β-Phenyl quenching of 9-phenylphenalenones: a novel photocyclisation reaction with biological implications." Phys. Chem. Chem. Phys. 16, no. 35 (2014): 18813–20. http://dx.doi.org/10.1039/c4cp02783c.

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23

Naito, Takeaki, Yumiko Hirata, Okiko Miyata, and Ichiya Ninomiya. "Photocyclisation of enamides. Part 27. Total syntheses of (±)-yohimbine, (±)-alloyohimbine, and (±)-19,20-didehydroyohimbines." J. Chem. Soc., Perkin Trans. 1, no. 8 (1988): 2219–25. http://dx.doi.org/10.1039/p19880002219.

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24

ATFAH, A., M. Y. ABU-SHUHEIL, and J. HILL. "ChemInform Abstract: Photocyclisation of 2-Aroylquinoxalines; Formation of Coloured Indolo( 1,2-a)quinoxalines." ChemInform 22, no. 1 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199101243.

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25

Febvay, Julie, Charles S. Demmer, Pascal Retailleau, Jeanne Crassous, Laura Abella, Jochen Autschbach, Arnaud Voituriez, and Angela Marinetti. "Phosphahelicenes with (Thio)Phosphinic Acid and Ester Functions by the Oxidative Photocyclisation Approach." Chemistry – A European Journal 25, no. 68 (December 5, 2019): 15609–14. http://dx.doi.org/10.1002/chem.201903750.

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26

Griesbeck, Axel, Peter Cygon, and Johann Lex. "Stereoselective Synthesis of 3-Alkylated cis-1,2-Cyclobutanediols and Derivatives by Norrish-Yang Photocyclisation." Letters in Organic Chemistry 1, no. 4 (October 1, 2004): 313–15. http://dx.doi.org/10.2174/1570178043400613.

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27

Edtmüller, Verena, Alexander Pöthig, and Thorsten Bach. "Enantioselective photocyclisation reactions of 2-aryloxycyclohex-2-enones mediated by a chiral copper-bisoxazoline complex." Tetrahedron 73, no. 33 (August 2017): 5038–47. http://dx.doi.org/10.1016/j.tet.2017.05.005.

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28

Austin, Mark, Oliver J. Egan, Raymond Tully, and Albert C. Pratt. "Quinoline synthesis: scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes." Organic & Biomolecular Chemistry 5, no. 23 (2007): 3778. http://dx.doi.org/10.1039/b711620a.

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29

Kamboj, Ramesh C., Geeta Sharma, Dinesh Kumar, and Rita Arora. "Photocyclisation of 3-alkoxy-6-chloro-2-(3-methylthiophen-2-yl)-4H-chromen-4-ones." Comptes Rendus Chimie 15, no. 4 (April 2012): 311–16. http://dx.doi.org/10.1016/j.crci.2011.11.005.

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30

Kamboj, Ramesh C., Urmila Berar, Surinder Berar, Zeba N. Siddiqui, and Satish C. Gupta. "Photochemistry of 3-alkoxychromones: photocyclisation of 2-aryl-6-chloro-3-{(thiophen-2-yl)methoxy}chromones." Journal of the Brazilian Chemical Society 21, no. 2 (2010): 270–78. http://dx.doi.org/10.1590/s0103-50532010000200012.

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31

Gramain, Jean-Claude, Yves Troin, and Danielle Vallée-Goyet. "Photocyclisation de N-aroylenamines derivees d'acides carboxyliques heteroaromatiques. Syntheses de spirocyclohexyl piperidines accolees a un heterocycle." Tetrahedron 47, no. 35 (August 1991): 7301–8. http://dx.doi.org/10.1016/s0040-4020(01)89732-5.

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32

Ashraf, M. Arfan, Matthew A. Jones, Natalie E. Kelly, Alex Mullaney, John S. Snaith, and Iwan Williams. "Synthesis and photolysis studies of carboxylic esters of 2-hydroxy-1,2,2-triphenylethanone: a novel tandem photocyclisation." Tetrahedron Letters 44, no. 15 (April 2003): 3151–54. http://dx.doi.org/10.1016/s0040-4039(03)00513-6.

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33

Naito, Takeaki, Noriko Kojima, Okiko Miyata, Ichiya Ninomiya, Masatoshi Inoue, and Mitsunobu Doi. "Photocyclisation of enamides. Part 29. A general strategy for the synthesis of ipecac and heteroyohimbine alkaloids." Journal of the Chemical Society, Perkin Transactions 1, no. 5 (1990): 1271. http://dx.doi.org/10.1039/p19900001271.

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34

Hayward, John J., Roger Gumbau-Brisa, Antonio Alberola, Caroline S. Clarke, Jeremy M. Rawson, and Melanie Pilkington. "An unusual single-crystal-to-single-crystal [2 + 2] photocyclisation reaction of a TTF-arylnitrile derivative." CrystEngComm 16, no. 31 (2014): 7268–77. http://dx.doi.org/10.1039/c4ce00346b.

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35

ter Halle, Alexandra, Agnès Piquet, and Claire Richard. "An actual scenario that demonstrates sulcotrione photodegradation on maize leaves after spraying." Environmental Chemistry 4, no. 4 (2007): 256. http://dx.doi.org/10.1071/en07028.

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Environmental context. Recent developments in environmental monitoring have revealed that pesticides are dispersed through all parts of the environment. Air, water and soil are all contaminated. In this context there are tightening regulations on pesticide use with the goal of limiting their environmental impact. We look here at how pesticides can actually break down very quickly after their application on leaves, due to the effect of sunlight, i.e. ‘photodegradation’. Understanding this phenomenon could help to reduce application rates. Abstract. The fate of sulcotrione (a pesticide and herbicide) has been monitored on maize leaves after spraying. One hour after spraying, 10% of the active ingredient is already transformed by the action of solar light. Sulcotrione mainly undergoes photocyclisation. The photoproduct, which has been fully characterised, is easily detected on the leaf surface. The day after spraying, 90% of the sulcotrione initially detected has disappeared. Twenty three percent is detected as the cyclisation product. Two days after spraying sulcotrione is no longer detected but the photoproduct still represents 7% of the initial amount detected. This study brings out the importance of the photodegradation pathway after crop spraying.

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36

Toda, Fumio, and Hisakazu Miyamoto. "Formation of chiral β-lactams by photocyclisation of achiral N,N-diisopropylarylglyoxylamides in their chiral crystalline form." J. Chem. Soc., Perkin Trans. 1, no. 10 (1993): 1129–32. http://dx.doi.org/10.1039/p19930001129.

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37

Aoyama, Hiromu, Yoshiaki Arata, and Yoshimori Omote. "Photocyclisation of γ,δ- and δ, Îµ-unsaturated amines. Hydrogen transfer reactions via eight-membered cyclic transition states." J. Chem. Soc., Chem. Commun., no. 20 (1985): 1381–82. http://dx.doi.org/10.1039/c39850001381.

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38

Toda, Fumio, Minoru Yagi, and Shin-ichi Sōda. "Formation of a chiral β-lactam by photocyclisation of an achiral oxo amide in its chiral crystalline state." J. Chem. Soc., Chem. Commun., no. 18 (1987): 1413–14. http://dx.doi.org/10.1039/c39870001413.

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39

Marjory Close, Edmund J. Haws, Christopher J. Perry, and John D. Coyle. "The Reactions of ω-Hydroxylactams obtained from the Photocyclisation of Dicarboximide Mannich Bases: a Route to Substituted Imidazoles." Journal of Chemical Research, no. 4 (1997): 115. http://dx.doi.org/10.1039/a607266f.

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40

Kamboj, Ramesh C., Urmila Berar, Surinder Berar, Mandeep Thakur, Rita Arora, and Satish C. Gupta. "Photochemistry of 3-alkoxychromones I — Photocyclisation of 6-chloro-3-alkoxy-2-(furan-3-yl)-4H-chromen-4-ones." Canadian Journal of Chemistry 87, no. 2 (February 2009): 422–29. http://dx.doi.org/10.1139/v08-177.

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3-Alkoxy/allyloxy-6-chloro-2-(furan-3-yl)-4H-chromen-4-ones yield angular tetracyclic products involving the 2-furyl group on photoirradiation through the intermediacy of 1,4-biradicals. The nature of the 3-alkoxy/allyloxy group influenced the photoproduct distribution. The stereochemical dispositions of the products have been established using the J/Φ relationship and were corroborated by MM2 calculations.

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41

Jones, Robert J., and Michael P. Cava. "Photocyclisation strategy for the synthesis of antitumour agent CC-1065: synthesis of thiophene analogues of PDE-I and PDE-II." Journal of the Chemical Society, Chemical Communications, no. 11 (1986): 826. http://dx.doi.org/10.1039/c39860000826.

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42

Brown, David, Michael G. B. Drew, and John Mann. "Intramolecular photocyclisation reactions of 5-tert-butyldimethylsilyloxymethyl-3-(3-formylpropyl)furan-2(5H )-one: formation of bicyclic and spirobicyclic lactones." Journal of the Chemical Society, Perkin Transactions 1, no. 24 (1997): 3651–56. http://dx.doi.org/10.1039/a703745g.

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43

Tanaka, Koichi, Osamu Kakinoki, and Fumio Toda. "Control of the stereochemistry in the photocyclisation of acrylanilides to 3,4-dihydroquinolin-2(1H)-ones. Delicate dependence on the host compound." Journal of the Chemical Society, Chemical Communications, no. 15 (1992): 1053. http://dx.doi.org/10.1039/c39920001053.

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44

Troin, Y., J. C. Gramain, and T. Prangé. "Structure de l'hydroxy-6 phényl-6 aza-1 bicyclo[3.2.0]heptanone-2, C12H13NO2, produit de photocyclisation de la N-phénacyl pyrrolidone-2." Acta Crystallographica Section C Crystal Structure Communications 41, no. 7 (July 15, 1985): 1093–95. http://dx.doi.org/10.1107/s0108270185006710.

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45

Grainger, Richard S., Richard J. Boxall, and Leigh Ferris. "Synthesis of C-13 Oxidised Cuparene and Herbertane Sesquiterpenes via a Paternò-Büchi Photocyclisation-Oxetane Fragmentation Strategy: Total Synthesis of 1,13-Herbertenediol." Synlett, no. 13 (2004): 2379–81. http://dx.doi.org/10.1055/s-2004-832813.

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46

Leo, Edgar A., Rosa Tormos, and Miguel A. Miranda. "Enhanced reactivity in OH/NH/? polyfunctional systems through coupled proton/electron transfer in the excited state: the photocyclisation of 2-allyl-3-aminophenol." Chemical Communications, no. 9 (2005): 1203. http://dx.doi.org/10.1039/b416625f.

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47

Du, Yong, Jiadan Xue, Ming-De Li, Xiangguo Guan, David W McCamant, and David Lee Phillips. "Unravelling the Reaction Mechanism for the Fast Photocyclisation of 2-Benzoylpyridine in Aqueous Solvent by Time-Resolved Spectroscopy and Density Functional Theory Calculations." Chemistry - A European Journal 16, no. 23 (April 30, 2010): 6961–72. http://dx.doi.org/10.1002/chem.200903073.

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48

Ninomiya, Ichiya, Naoko Habe (née Kuninobu), Toshiko Kiguchi, and Takeaki Naito. "Photocyclisation of enamides. Part 35. New total syntheses of the ergot alkaloids (±)-chanoclavine-1 and (±)-isochanoclavine-I using a fragmentation of 3-amino alcohols." J. Chem. Soc., Perkin Trans. 1, no. 12 (1991): 3275–85. http://dx.doi.org/10.1039/p19910003275.

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49

Naito, Takeaki, Yoko Yuumoto, Toshiko Kiguchi, and Ichiya Ninomiya. "Photocyclisation of enamides. Part 39. General strategy for the synthesis of pseudodistomins: synthesis of triacetates of (±)-tetrahydropseudodistomin and proposed structures of pseudodistomins A and B." J. Chem. Soc., Perkin Trans. 1, no. 3 (1996): 281–88. http://dx.doi.org/10.1039/p19960000281.

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50

Kohmoto, Shigeo, Takashi Kobayashi, Takehiko Nishio, Ikuo Iida, Keiki Kishikawa, Makoto Yamamoto, and Kazutoshi Yamada. "Inter- and intra-molecular selectivity in the cyclisation of N-cinnamoyl-1-naphthamides in solid-state photochemistry and peri selectivity in their photocyclisation in solution." Journal of the Chemical Society, Perkin Transactions 1, no. 6 (1996): 529. http://dx.doi.org/10.1039/p19960000529.

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