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Journal articles on the topic 'Di-π-methane rearrangement'

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Published: 4 June 2021

Last updated: 11 February 2022

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1

Zimmerman, Howard E. "ChemInform Abstract: Di-π-Methane Rearrangement". ChemInform 43, № 39 (2012): no. http://dx.doi.org/10.1002/chin.201239272.

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2

Nair, Vijay, Gopinathan Anilkumar, Jaya Prabhakaran, Davis Maliakal, Guenter K. Eigendorf та Paul G. Williard. "Photochemical di-π-methane rearrangement of quinoxalinobarrelenes". Journal of Photochemistry and Photobiology A: Chemistry 111, № 1-3 (1997): 57–59. http://dx.doi.org/10.1016/s1010-6030(97)00256-6.

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3

ZIMMERMAN, H. E. "ChemInform Abstract: The Di-π-methane Rearrangement". ChemInform 23, № 38 (2010): no. http://dx.doi.org/10.1002/chin.199238310.

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4

Zimmerman, Howard E., та Diego Armesto. "Synthetic Aspects of the Di-π-methane Rearrangement". Chemical Reviews 96, № 8 (1996): 3065–112. http://dx.doi.org/10.1021/cr910109c.

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5

Rigo, Massimo, Manuela Weber, and Christian Müller. "Expanding the phosphorus–carbon analogy: formation of an unprecedented 5-phosphasemibullvalene derivative." Chemical Communications 52, no. 44 (2016): 7090–93. http://dx.doi.org/10.1039/c6cc02461k.

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6

ZIMMERMAN, H. E., та D. ARMESTO. "ChemInform Abstract: Synthetic Aspects of the Di-π-methane Rearrangement". ChemInform 28, № 14 (2010): no. http://dx.doi.org/10.1002/chin.199714325.

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7

Schlosser, Julika, Radek Cibulka, Philipp Groß, Heiko Ihmels та Christian J. Mohrschladt. "Visible‐Light‐Induced Di‐π‐Methane Rearrangement of Dibenzobarrelene Derivatives". ChemPhotoChem 4, № 2 (2019): 132–37. http://dx.doi.org/10.1002/cptc.201900221.

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8

Bender, Christopher Owen, Douglas Dolman, Jeremy Christian Foesier, Sherry Lee Lawson, and Kathryn Elvia Preuss. "The differing mechanisms of photo-formation of 7-cyanobenzocyclooctatetraene from 7- and 6-cyano-2,3-benzobicyclo[4.2.0]octa-2,4,7-triene." Canadian Journal of Chemistry 81, no. 1 (2003): 37–44. http://dx.doi.org/10.1139/v02-204.

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It is known that 7-cyanobenzocyclooctatetraene (COT 2) is a product of the thermolysis and direct photolysis of 7- and 6-cyano-2,3-benzobicyclo[4.2.0]octa-2,4,7-triene (1 and 5), though the mechanisms of these rearrangements have not been reported. In the present study experiments have been carried out using the deuterium-labelled trienes 1a (93%-d1 at C-6) and 5a (93%-d1 at C-8), which were formed from 2π + 2π photo-closure (direct irradiation) of COT 2a labelled at C-8. The results reveal that whereas the thermolysis of 1a and 5a and the direct irradiation of 5a reform COT 2a, probably via c

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9

Tanifuji, Naoki, Honghua Huang, Yoko Shinagawa та Keiji Kobayashi. "The di-π-methane rearrangement induced in tris(2-benzo[b]thienyl)methane". Tetrahedron Letters 44, № 4 (2003): 751–54. http://dx.doi.org/10.1016/s0040-4039(02)02713-2.

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10

Ihmels, Heiko, та Jia Luo. "Synthesis of cationic dibenzosemibullvalene-based phase-transfer catalysts by di-π-methane rearrangements of pyrrolinium-annelated dibenzobarrelene derivatives". Beilstein Journal of Organic Chemistry 7 (26 січня 2011): 119–26. http://dx.doi.org/10.3762/bjoc.7.17.

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Dibenzobarrelene derivatives, that are annelated with a pyrrolinium unit [N,N-dialkyl-3,4-(9',10'-dihydro-9',10'-anthraceno-3-pyrrolinium) derivatives], undergo a photo-induced di-π-methane rearrangement upon triplet sensitization to give the corresponding cationic dibenzosemibullvalene derivatives [N,N-dialkyl-3,4-{8c,8e-(4b,8b-dihydrodibenzo[a,f]cyclopropa[cd]pentaleno)}pyrrolidinium derivatives]. Whereas the covalent attachment of a benzophenone functionality to the pyrrolinium nitrogen atom did not result in an internal triplet sensitization, the introduction of a benzophenone unit as part

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11

Tröster, Andreas, та Thorsten Bach. "Triplet-sensitised di-π-methane rearrangement of N-substituted 2-azabarrelenones". Chemical Communications 55, № 3 (2019): 302–5. http://dx.doi.org/10.1039/c8cc08704k.

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When irradiated at λ = 366 nm or at λ = 420 nm in the presence of an appropriate sensitiser the title compounds underwent a di-π-methane rearrangement which led to the formation of tricyclic azasemibullvalenones (2a,2a<sup>1</sup>,2b,4a-tetrahydroazacyclopropa[cd]pentalenones) in yields of 63–87%.

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12

Budac., David, and Peter Wan. "Excited state carbon acid dissociation and competing photorearrangements of 5H-dibenzo[a,c]cycloheptene derivatives." Canadian Journal of Chemistry 74, no. 8 (1996): 1447–64. http://dx.doi.org/10.1139/v96-162.

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The first examples of dissociating excited state carbon acids were reported by our group. A necessary structural feature is the 5H-dibenzocycloheptene ring system where the incipient carbanion is formally an antiaromatic system in S0. In this work, structure–reactivity studies of the excited singlet state carbon acid dissociation and competing formal di-π-methane rearrangement of several 5H-dibenzo[a,c]cycloheptene derivatives have been carried out in order to gain more insights into the photochemistry displayed by these compounds. Photolysis of 7-deuterio-5H-dibenzo[a,c]cycloheptene (9) in aq

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13

Bender, Christopher Owen, and Douglas Dolman. "The photochemistry of 5-cyano-2,3-benzobicyclo[4.2.0]octa-2,4,7-triene." Canadian Journal of Chemistry 67, no. 1 (1989): 82–87. http://dx.doi.org/10.1139/v89-014.

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The direct irradiation of 5-cyano-2,3-benzobicyclo[4.2.0]octa-2,4,7-triene (18) led to 6-cyanobenzocyclooctatetraene (17; Φ = 0.00075), 6-cyanobenzosemibullvalene (14; Φ = 0.0003), and 2-cyanonaphthalene (Φ = 0.00015). The triplet excited state of 18, generated by sensitization with a variety of ketone sensitizers (e.g., Michler's ketone and acetophenone), showed no unimolecular reactivity. Compound 18 does not participate in Zimmerman di-π-methane rearrangement; the potential product from such a transformation, 8-cyanobenzosemibullvalene (19), was, however, isolated from direct (Corex filter;

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14

Armesto, Diego, Ana Ramos та Elena P. Mayoral. "The aza-di-π-methane rearrangement of β-γ-unsaturated oximes". Tetrahedron Letters 35, № 22 (1994): 3785–88. http://dx.doi.org/10.1016/s0040-4039(00)73099-1.

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15

Cox, Jason R., Jeffrey H. Simpson та Timothy M. Swager. "Photoalignment Layers for Liquid Crystals from the Di-π-methane Rearrangement". Journal of the American Chemical Society 135, № 2 (2013): 640–43. http://dx.doi.org/10.1021/ja312090p.

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16

McClure, Cynthia K., Anthony J. Kiessling та Jeffrey S. Link. "Oxa-di-π-methane Photochemical Rearrangement of Quinuclidinones. Synthesis of Pyrrolizidinones". Organic Letters 5, № 21 (2003): 3811–13. http://dx.doi.org/10.1021/ol035202p.

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17

Zimmerman, Howard E., та Wensheng Chen. "The Diverted Di-π-Methane Rearrangement; Mechanistic and Exploratory Organic Photochemistry1". Organic Letters 4, № 7 (2002): 1155–58. http://dx.doi.org/10.1021/ol025564h.

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18

Armesto, Diego, William M. Horspool, Fernando Langa та Rafael Perez-Ossorio. "Substitution effects on the aza-di-π-methane rearrangement of imines". J. Chem. Soc., Perkin Trans. 2, № 8 (1987): 1039–42. http://dx.doi.org/10.1039/p29870001039.

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19

Dura, Robert D., та Leo A. Paquette. "Ring Contraction of Bridgehead Sultams by Photoinduced Di-π-methane Rearrangement". Journal of Organic Chemistry 71, № 6 (2006): 2456–59. http://dx.doi.org/10.1021/jo0526587.

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20

Armesto, Diego, Maria J. Ortiz та Santiago Ramano. "The oxa-di-π-methane rearrangement of β,γ-unsaturated aldehydes". Tetrahedron Letters 36, № 6 (1995): 965–68. http://dx.doi.org/10.1016/0040-4039(94)02402-w.

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21

Frutos, Luis M., Unai Sancho та Obis Castaño. "Triplet versus Singlet Photoreaction Mechanism in the Barrelene Di-π-methane Rearrangement". Organic Letters 6, № 8 (2004): 1229–31. http://dx.doi.org/10.1021/ol049977p.

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22

Matute, Ricardo A., та Kendall N. Houk. "The Triplet Surface of the Zimmerman Di-π-Methane Rearrangement of Dibenzobarrelene". Angewandte Chemie International Edition 51, № 52 (2012): 13097–100. http://dx.doi.org/10.1002/anie.201208002.

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23

Rao, V. Jayathirtha, та Kolupula Srinivas. "ChemInform Abstract: Oxa-di-π-Methane Rearrangement of β,γ-Unsaturated Ketones". ChemInform 43, № 39 (2012): no. http://dx.doi.org/10.1002/chin.201239271.

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24

Matute, Ricardo A., та Kendall N. Houk. "The Triplet Surface of the Zimmerman Di-π-Methane Rearrangement of Dibenzobarrelene". Angewandte Chemie 124, № 52 (2012): 13274–77. http://dx.doi.org/10.1002/ange.201208002.

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25

Bender, Christopher Owen, Dean Sutherland Clyne, and Douglas Dolman. "The photochemistry of 1-cyano-2,3-benzobicyclo[4.2.0]octa-2,4,7-triene." Canadian Journal of Chemistry 69, no. 1 (1991): 70–76. http://dx.doi.org/10.1139/v91-010.

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The title compound (10) was prepared, along with the 4-cyano isomer (11), by the direct irradiation of 5-cyanobenzocyclooctatetraene (9); the yields were 82% (Φ10 = 0.0030) and 12% (Φ11 = 0.0004) respectively. Triene 10 was thermally and photochemically reactive. Heating solutions of 10 at 150 °C for 1 h gave COT 9 quantitatively. On direct irradiation 10 forms 5-cyanobenzosemibullvalene (12; 5%, Φ = 0.019), COT 9 (70%, Φ = 0.56), and 1-cyanonaphthalene (14%, Φ = 0.078). Sensitized irradiation of 10 gave 9 exclusively (92%, Φ = 0.88). COT 9 was also produced by the direct irradiation of semibu

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26

Asplund, Charlotte Lee, Christopher Owen Bender, and Douglas Dolman. "The photochemistry of 2,3-benzobicyclo[4.2.0]octa-2,4,7-triene." Canadian Journal of Chemistry 72, no. 9 (1994): 1999–2004. http://dx.doi.org/10.1139/v94-255.

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2,3-Benzobicyclo[4.2.0]octa-2,4,7-triene (11) was prepared by Shapiro reaction from 2,3-benzobicyclo[4.2.0]octa-2,7-dien-4-one (10). Triene 11 was found to be thermally and photochemically reactive. Benzocyclooctatetraene (i.e., COT 12) was the unique product formed when solutions of 11 were heated at 150 °C for 5.5 h. The direct irradiation of triene 11 gave benzosemibullvalene (i.e., SB 14, 23%, Φ = 0.069), COT 12 (39%, Φ = 0.11), and naphthalene (8%, Φ = 0.025). Sensitized irradiations of 11 gave SB 14, (54%, Φ = 0.082), COT 12 (2%, Φ = 0.003), and naphthalene (4%, Φ = 0.009). Studies with

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27

ARMESTO, D., M. J. ORTIZ та S. ROMANO. "ChemInform Abstract: The Oxa-di-π-methane Rearrangement of β,γ-Unsaturated Aldehydes." ChemInform 26, № 24 (2010): no. http://dx.doi.org/10.1002/chin.199524052.

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28

Bruce, Marlene, Martin Papke, Andreas W. Ehlers та ін. "Pyridyl‐Functionalized 1‐Phosphabarrelene: Synthesis, Coordination Chemistry and Photochemical di‐π‐Methane Rearrangement". Chemistry – A European Journal 25, № 63 (2019): 14332–40. http://dx.doi.org/10.1002/chem.201903344.

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29

Jiménez-Osés, Gonzalo, Peng Liu, Ricardo A. Matute та Kendall N. Houk. "Competition Between Concerted and Stepwise Dynamics in the Triplet Di-π-Methane Rearrangement". Angewandte Chemie International Edition 53, № 33 (2014): 8664–67. http://dx.doi.org/10.1002/anie.201310237.

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30

Jiménez-Osés, Gonzalo, Peng Liu, Ricardo A. Matute та Kendall N. Houk. "Competition Between Concerted and Stepwise Dynamics in the Triplet Di-π-Methane Rearrangement". Angewandte Chemie 126, № 33 (2014): 8808–11. http://dx.doi.org/10.1002/ange.201310237.

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31

Margetic, Davor, Douglas N. Butler, and Ronald N. Warrener. "Photolysis of Fused Cyclobutatriazolines: An Adventitious Route to 3,6-Di(2-pyridyl)pyridazonorbornadiene." Australian Journal of Chemistry 53, no. 12 (2000): 959. http://dx.doi.org/10.1071/ch00129.

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Ultraviolet irradiation of the triazolines (18a,b) formed by the high-pressure addition of benzyl azide to dimethyl 3,6-di(2-pyridyl)-4,5-diazatetracyclo[6.4.1.0 2,3 .0 9,12 ]trideca-3,5,7,10-tetraene-10,12-dicarboxylate (16a) and the related monoester (16b), forms 13–17% of the expected aziridine (19a,b), together with cyclobutane-cleavage products that include the hitherto unknown pyridazinonorbornadiene (2), its di-π-methane rearrangement product (21) and the corresponding triazoles (20a,b). Mechanistic pathways are discussed.

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32

Bender, Christopher Owen. "Mechanistic variations in the formation of benzocyclooctatetraene from benzobicyclo[4.2.0]octa-2,4,7-triene." Canadian Journal of Chemistry 74, no. 1 (1996): 32–37. http://dx.doi.org/10.1139/v96-004.

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Benzocyclooctatetraene (i.e., COT, 2) is the major product from the thermolysis and direct photolysis of 2,3-benzobicyclo[4.2.0]octa-2,4,7-triene (i.e., triene 1). It is also a minor product from the sensitized irradiation of 1. The mechanism of the reaction 1 → 2 was investigated using deuterium-labelled triene (i.e., 1a/b), which was prepared in a two-step procedure from a known triene mixture (1a) containing deuterium at both C-4 (43%) and C-5 (97%): the thermolysis of 1a led to labelled COT 2a, which upon direct irradiation (λ ≥ 310 nm) gave the deuterated triene mixture 1a/b in good chemi

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33

Matute, Ricardo A., Patricia Pérez, Eduardo Chamorro та ін. "Reaction Electronic Flux Perspective on the Mechanism of the Zimmerman Di-π-methane Rearrangement". Journal of Organic Chemistry 83, № 11 (2018): 5969–74. http://dx.doi.org/10.1021/acs.joc.8b00499.

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34

Singh, Vishwakarma, та Bhupathiraju N. S. Raju. "π4s+ π2sCycloaddition: Synthesis and OXA-DI-π-Methane Rearrangement of Annulated Bicyclo (2.2.2) Octenones". Synthetic Communications 18, № 13 (1988): 1513–24. http://dx.doi.org/10.1080/00397918808081308.

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35

Michael Corbett, R., Chee-Seng Lee, Michelle M. Sulikowski, Joseph Reibenspies та Gary A. Sulikowski. "Application of the oxa-di-π-methane photoisomerization in the rearrangement of carbocycles possessing bridgehead unsaturation". Tetrahedron 53, № 32 (1997): 11099–108. http://dx.doi.org/10.1016/s0040-4020(97)00369-4.

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36

Mori, Yukie, та Keiko Takano. "Reaction mechanism of di-π-methane rearrangement of 4-phenyl-4H-pyran: A CASSCF/MRMP2 study". Journal of Photochemistry and Photobiology A: Chemistry 219, № 2-3 (2011): 278–84. http://dx.doi.org/10.1016/j.jphotochem.2011.03.004.

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37

Armesto, Diego, William M. Horspool, Maria J. Mancheño та Maria J. Ortiz. "The aza-di-π-methane rearrangement of stable derivatives of 2,2-dimethyl-4,4-diphenylbut-3-enal". J. Chem. Soc., Perkin Trans. 1, № 8 (1990): 2348–49. http://dx.doi.org/10.1039/p19900002348.

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38

Mehta, Goverdhan, та Duvvuri Subrahmanyam. "Photochemical oxa-di-π-methane rearrangement approach to [3.3.3]propellanes. Total synthesis of sesquiterpene hydrocarbon (±)-modhephene". J. Chem. Soc., Perkin Trans. 1, № 2 (1991): 395–401. http://dx.doi.org/10.1039/p19910000395.

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39

Armesto, Diego, William M. Horspool та Fernando Langa. "The Aza-di-π-methane rearrangement of O-acetyl 2,2-dimethyl-4,4-diphenylbut-3-enal oxime". J. Chem. Soc., Chem. Commun., № 24 (1987): 1874–75. http://dx.doi.org/10.1039/c39870001874.

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40

Scheffer, John R., and Kodumuru Vishnumurthy. "The photochemistry of trans-1,4,4,4-tetraphenyl-but-2-en-1-one: A highly efficient aryl migration (type B) enone photorearrangement." Canadian Journal of Chemistry 81, no. 6 (2003): 705–8. http://dx.doi.org/10.1139/v03-030.

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Photolysis of trans-1,4,4,4-tetraphenylbut-2-en-1-one (3) in acetonitrile or benzene leads to transcis isomerization (7) along with rearrangement to trans-1-benzoyl-2,2,3-triphenylcyclopropane (8). Formation of the latter product represents a new example of the aryl migration (type B) enone photorearrangement reaction first reported by Zimmerman and co-workers for 4,4-diphenylcyclohex-2-en-1-one (1). The quantum yield in the case of enone 3 (0.4) is approximately 10 times greater than that for 4,4,-diphenylcyclohex-2-en-1-one, a result that is ascribed to steric acceleration of phenyl migrati

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41

Matute, Ricardo A., та Kendall N. Houk. "Innenrücktitelbild: The Triplet Surface of the Zimmerman Di-π-Methane Rearrangement of Dibenzobarrelene (Angew. Chem. 52/2012)". Angewandte Chemie 124, № 52 (2012): 13355. http://dx.doi.org/10.1002/ange.201209048.

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42

Armesto, Diego, Mar G. Gallego, William M. Horspool та Antonia R. Agarrabeitia. "A new photochemical synthesis of cyclopropanecarboxylic acids present in pyrethroids by the aza-di-π-methane rearrangement". Tetrahedron 51, № 33 (1995): 9223–40. http://dx.doi.org/10.1016/0040-4020(95)00527-f.

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43

Hemetsberger, Helfried, та Matthias Nobbe. "Substituent effects on the efficiencies and regioselectivities of the di-π-methane rearrangement of vinyl-substituted bicyclic systems". Tetrahedron 44, № 1 (1988): 67–80. http://dx.doi.org/10.1016/s0040-4020(01)85094-8.

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44

Singh, Vishwakarma, Punitha Vedantham та Pramod K. Sahu. "Reactive species from aromatics and oxa-di-π-methane rearrangement: a stereoselective synthesis of (±)-hirsutene from salicyl alcohol". Tetrahedron 60, № 37 (2004): 8161–69. http://dx.doi.org/10.1016/j.tet.2004.06.096.

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45

Ünaldi, Nermin S., та Metin Balci. "Substituent effect on regioselectivity in the di-π-methane rearrangement: synthesis of disubstituted benzobarrelene derivatives and their photochemistry". Tetrahedron Letters 42, № 47 (2001): 8365–67. http://dx.doi.org/10.1016/s0040-4039(01)01770-1.

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46

Kuan, Kai-Yuan, та Daniel A. Singleton. "Vibrationally Hot and Cold Triplets. Sensitizer-Dependent Dynamics and Localized Vibrational Promotion of a Di-π-methane Rearrangement". Journal of the American Chemical Society 142, № 47 (2020): 19885–88. http://dx.doi.org/10.1021/jacs.0c10468.

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47

Li, Xin, Tao Liao та Lung Wa Chung. "Computational Prediction of Excited-State Carbon Tunneling in the Two Steps of Triplet Zimmerman Di-π-Methane Rearrangement". Journal of the American Chemical Society 139, № 46 (2017): 16438–41. http://dx.doi.org/10.1021/jacs.7b07539.

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48

CORBETT, R. M., C. S. LEE, M. M. SULIKOWSKI, J. REIBENSPIES та G. A. SULIKOWSKI. "ChemInform Abstract: Application of the Oxa-di-π-methane Photoisomerization in the Rearrangement of Carbocycles Possessing Bridgehead Unsaturation." ChemInform 28, № 52 (2010): no. http://dx.doi.org/10.1002/chin.199752095.

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49

MEHTA, G., та D. SUBRAHMANYAM. "ChemInform Abstract: Photochemical Oxa-di-π-methane Rearrangement Approach to (3.3.3) Propellanes. Total Synthesis of Sesquiterpene Hydrocarbon (.+-.)- Modhephene." ChemInform 22, № 18 (2010): no. http://dx.doi.org/10.1002/chin.199118256.

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50

Bender, Christopher Owen, Douglas Dolman, and Gaetanne Kathryn Murphy. "The photochemistry of 8-cyano-2,3-benzobicyclo[4.2.0]octa-2,4,7-triene." Canadian Journal of Chemistry 66, no. 7 (1988): 1656–62. http://dx.doi.org/10.1139/v88-269.

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The direct irradiation of 6-cyanobenzocyclooctatetraene (7) led to 5- and 8-cyano-2,3-benzobicyclo[4.2.0]octa-2,4,7-triene (9 and 8), isolated in 21 and 63% yields, respectively. On triplet sensitized irradiation 8 gave 1- and 6-cyanobenzosemi-bullvalenes (4 and 12; Φ = 0.006 and 0.088, respectively) and naphthalene (Φ = 0.012). The direct irradiation of 8 yielded 12 (Φ = 0.050), naphthalene (Φ = 0.015), 7 (Φ = 0.007), 7-cyanobenzocyclooctatetraene (13; Φ = 0.007), and 5-cyano-7,8-benzotetracyclo[3.3.0.02,4.03,6]oct-7-ene (14; Φ = 0.004). Deuterium labelling studies suggest that 12 derives fro

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