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Journal articles on the topic 'Cycloheptatrienes'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

Nubbemeyer, Udo, Analuisa Nava, Lukas Trippe, Andrea Frank, Lars Andernach, and Till Opatz. "Synthesis of Optically Active Hydroxyalkyl Cycloheptatrienes: A Key Step in the Total Synthesis of 6,11-Methylene-LXB4." Synlett 32, no. 01 (2020): 45–50. http://dx.doi.org/10.1055/s-0040-1707282.

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AbstractStarting from methyl cycloheptatrienyl-1-carboxylate, 6-acylation was successfully achieved employing glutaryl chloride in the presence of AlCl3 under controlled reaction conditions to furnish keto carboxylic acid product. After protection of this keto carboxylic acid as tert-butyl ester, reagent-controlled enantioselective reductions delivered configuration-defined methyl-6-hydroxylalkyl cycloheptatriene-1-carboxylates with up to 80% ee. Whereas simple NaBH4 reduction of the keto carboxylic acid and subsequent lactonization afforded a methyl-6-tetrahydropyranonyl cycloheptatriene-1-ca

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2

Kreiter, Cornelius G., Karl Heinz Franzreb, Wolfgang Michels, Ulrich Schubert, and Klaus Ackermann. "Gehinderte Ligandbewegungen in Übergangsmetallkomplexen, XXVIII [1] Photochemische C–H-Aktivierung an 1,3,5-Cycloheptatrien durch Rhenium(O) / Hindered Ligand Movements in Transition Metal Complexes, XXVIII [1] Photochemical C–H-Activation at 1,3,5-Cycloheptatriene by Rhenium(O)." Zeitschrift für Naturforschung B 40, no. 9 (1985): 1188–98. http://dx.doi.org/10.1515/znb-1985-0916.

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Decacarbonyl-dirhenium(O) (1) photochemically cleaves C-H-bonds in 1,3,5-cycloheptatriene (2 ) and forms two isomeric Re2(CO)8(μ-H)(μ-η2:1-cycloheptatrienyl) complexes (3, 4). In addition Re(CO)3(η5-cycloheptatrienyl) (5) and Re(CO)3(η5-cycloheptadienyl) (6) are obtained. The complexes 3 and 4 show temperature dependent 1H NMR spectra due to hindered ligand movements of the cycloheptatrienyl bridges with activation barriers of ⊿G≠207 = 39.9±2 kJ mol-1 and ⊿G≠255 = 48.0±2 kJ mol-1. 3 and 4 achieve in a thermal reaction an equilibrium with populations of 0.03 and 0.97 at 350 K with ⊿G≠350 - 96.5

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3

Bajorek, T., and N. H. Werstiuk. "UV photoelectron spectroscopic and computational study of 7-substituted cycloheptatrienes." Canadian Journal of Chemistry 86, no. 5 (2008): 444–50. http://dx.doi.org/10.1139/v08-041.

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The He(I) photoelectron (PE) spectra of cycloheptatriene (1), 7-methylcycloheptatriene (2), 7-methoxycycloheptatriene (3), 7-methylthiocycloheptatriene (4), and 7-diemthylaminocycloheptatriene (5) were recorded and interpreted using MO energies and ionization potentials acquired from B3PW91 calculations. Partial simulated PE spectra were in good agreement with the experimental results. The axial and equatorial conformers have distinct PE spectra as illustrated by simulation. The PE spectra of 2, 3, and 5 are representative of the equatorial conformers, while the PE spectrum of 4 was in accord

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4

Ter Borg, A. P., and H. Kloosterziel. "The chemistry of cycloheptatriene: Part X: Photochemical shift of hydrogen in cycloheptatrienes." Recueil des Travaux Chimiques des Pays-Bas 84, no. 2 (2010): 241–44. http://dx.doi.org/10.1002/recl.19650840211.

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5

ter Borg, A. P., H. Kloosterziel, and Y. L. Westphal. "The chemistry of cycloheptatriene. Part XIV: Hydrogen shifts in (4-Dimethylaminophenyl)cycloheptatrienes." Recueil des Travaux Chimiques des Pays-Bas 86, no. 5 (2010): 474–80. http://dx.doi.org/10.1002/recl.19670860502.

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6

Coşkun, Ahmet, Murat Güney, Arif Daştan, and Metin Balci. "Oxidation of some alkoxy-cycloheptatriene derivatives: unusual formation of furan and furanoids from cycloheptatrienes." Tetrahedron 63, no. 23 (2007): 4944–50. http://dx.doi.org/10.1016/j.tet.2007.03.145.

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7

ter Borg, A. P., E. Razenberg, and H. Kloosterziel. "The Chemistry of Cycloheptatriene Part XII: The thermal behaviour of substituted cycloheptatrienes: Preliminary communication." Recueil des Travaux Chimiques des Pays-Bas 84, no. 9 (2010): 1230–32. http://dx.doi.org/10.1002/recl.19650840914.

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8

Mishima, Masaaki, Tomomi Kinoshita, Yoshitaka Hattori, and Ken'ichi Takeuchi. "Gas-Phase Acidities of Cycloheptatrienes: Effects of Alkyl Groups on the Stability of Carbanions." European Journal of Mass Spectrometry 8, no. 5 (2002): 359–66. http://dx.doi.org/10.1255/ejms.499.

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The gas-phase acidities of 7-alkyl substituted cycloheptatrienes have been determined by Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometry using a proton-transfer equilibrium method, Δ G0acid (kJ mol−1): methyl 1520.0, ethyl 1516.7, n-propyl acid 1513.3, i-propyl 1512.1, n-butyl 1510.4. The effect of alkyl groups on the acidity of cycloheptatriene is linearly correlated with the polarizability parameters ( σα) of substituents, giving a ρα of–55.3 (kJ σ−1α unit). The magnitude of pa is half of that for RCH3 and is significantly larger than that for the fluorene series. These

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9

Grubert, L., D. Jacobi, and W. Abraham. "Electrochemical oxidation of aryl cycloheptatrienes." Journal für praktische Chemie 341, no. 7 (1999): 620–30. http://dx.doi.org/10.1002/(sici)1521-3897(199910)341:7<620::aid-prac620>3.0.co;2-s.

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10

Çelik, Murat, and Metin Balci. "The substituent effect on the cycloheptatriene-norcaradiene equilibrium. Reaction of singlet oxygen with substituted cycloheptatrienes." Arkivoc 2007, no. 8 (2006): 150–62. http://dx.doi.org/10.3998/ark.5550190.0008.814.

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11

Chen, Zhongfang, Haijun Jiao, Judy I. Wu, Rainer Herges, S. B. Zhang, and Paul von Ragué Schleyer. "Homobenzene: Homoaromaticity and Homoantiaromaticity in Cycloheptatrienes." Journal of Physical Chemistry A 112, no. 42 (2008): 10586–94. http://dx.doi.org/10.1021/jp802496m.

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12

Nakadaira, Yasuhiro, Ryuji Sato, and Hideki Sakurai. "Synthesis of stanna- and germa-cycloheptatrienes." Journal of Organometallic Chemistry 441, no. 3 (1992): 411–17. http://dx.doi.org/10.1016/0022-328x(92)80172-t.

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13

Lebœuf, David, Morgane Gaydou, Yahui Wang, and Antonio M. Echavarren. "Intermolecular reactions of gold(i)-carbenes with furans by related mechanisms." Org. Chem. Front. 1, no. 7 (2014): 759–64. http://dx.doi.org/10.1039/c4qo00130c.

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The intermolecular gold(i)-catalyzed reactions of propargyl carboxylates, 1,6-enynes, or 7-substituted 1,3,5-cycloheptatrienes with furans afford cyclopentenones, polyenes or polycyclic compounds by related mechanisms initiated by the electrophilic addition of gold(i) carbenes to furans followed by ring-opening.

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14

Chan, Chieh-Kai, Yi-Ling Chan, Yu-Lin Tsai, and Meng-Yang Chang. "Synthesis of polyoxygenated dibenzo[ a , e ]cycloheptatrienes." Tetrahedron 73, no. 15 (2017): 2074–88. http://dx.doi.org/10.1016/j.tet.2017.02.054.

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15

D’yakonov, V. A., G. N. Kadikova, D. I. Kolokol’tsev, L. M. Khalilov, and U. M. Dzhemilev. "Transition metal-catalyzed homodimerization of 1,3,5-cycloheptatrienes." Russian Chemical Bulletin 62, no. 2 (2013): 441–43. http://dx.doi.org/10.1007/s11172-013-0060-y.

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16

Goldschmidt, Zeev, Hugo E. Gottlieb, Amira Almadhoun, Metin Balci, and Yasar Demir. "Activation of electron deficient cycloheptatrienes by tricarbonyliron complexation." Tetrahedron Letters 31, no. 46 (1990): 6711–12. http://dx.doi.org/10.1016/s0040-4039(00)97154-5.

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17

Dyakonov, V. A., G. N. Kadikova, and U. M. Dzhemilev. "Transition metal complex-mediated chemistry of 1,3,5-cycloheptatrienes." Russian Chemical Reviews 87, no. 8 (2018): 797–820. http://dx.doi.org/10.1070/rcr4793.

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18

Schalk, Oliver, Andrey E. Boguslavskiy, Michael S. Schuurman, et al. "Substituent Effects on Dynamics at Conical Intersections: Cycloheptatrienes." Journal of Physical Chemistry A 117, no. 40 (2013): 10239–47. http://dx.doi.org/10.1021/jp309875m.

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19

Mormann, Michael, and Dietmar Kuck. "Protonated 1,3,5-cycloheptatriene and 7-alkyl-1,3,5-cycloheptatrienes in the gas phase: ring contraction to the isomeric alkylbenzenium ions." Journal of Mass Spectrometry 34, no. 4 (1999): 384–94. http://dx.doi.org/10.1002/(sici)1096-9888(199904)34:4<384::aid-jms770>3.0.co;2-8.

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20

Jacobi, Dirk, Werner Abraham, Uwe Pischel, Lutz Grubert, R. Stösser, and Wolfram Schnabel. "Oxidation of aryl-substituted cycloheptatrienes by photoinduced electron transfer." Journal of the Chemical Society, Perkin Transactions 2, no. 8 (1999): 1695–702. http://dx.doi.org/10.1039/a902662b.

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21

GOLDSCHMIDT, Z., H. E. GOTTLIEB, A. ALMADHOUN, M. BALCI, and Y. DEMIR. "ChemInform Abstract: Activation of Electron Deficient Cycloheptatrienes by Tricarbonyliron Complexation." ChemInform 23, no. 15 (2010): no. http://dx.doi.org/10.1002/chin.199215263.

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22

Borell, P. M., H. G. Löhmannsröben, and K. Luther. "Fast internal conversions of S1 cycloheptatrienes investigated by multiphoton ionization." Chemical Physics Letters 136, no. 3-4 (1987): 371–76. http://dx.doi.org/10.1016/0009-2614(87)80269-5.

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23

van Tilborg, W. J. M., P. Smael, J. P. Visser, C. G. Kouwenhoven, and D. N. Reinhoudt. "A novel method for the synthesis of specifically substituted cycloheptatrienes." Recueil des Travaux Chimiques des Pays-Bas 94, no. 4 (2010): 85–88. http://dx.doi.org/10.1002/recl.19750940405.

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24

Green, Malcolm L. H., Philip Mountford, Peter Scott, and Victor S. B. Mtetwa. "New cycloheptatriene and cycloheptatrienyl derivatives of niobium." Polyhedron 10, no. 3 (1991): 389–92. http://dx.doi.org/10.1016/s0277-5387(00)80161-8.

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25

Picotin, G., and Ph Miginiac. "Synthesis of 7-alkyl-cycloheptatrienes from allylic silanes and tropylium tetrafluoroborate." Tetrahedron Letters 29, no. 46 (1988): 5897–98. http://dx.doi.org/10.1016/s0040-4039(00)82219-4.

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26

Sengül, M. Emin, Zeynep Ceylan, and Metin Balci. "Unusual triethylamine catalyzed rearrangement of bicyclic endoperoxides derived from substituted cycloheptatrienes." Tetrahedron 53, no. 30 (1997): 10401–8. http://dx.doi.org/10.1016/s0040-4020(97)00630-3.

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27

Holmeide, Anne Kristin, and Lars Skattebøl. "Formation of cycloheptatrienes by alkyllithium induced cyclisation of polyunsaturated enol ethers." Tetrahedron Letters 48, no. 8 (2007): 1357–58. http://dx.doi.org/10.1016/j.tetlet.2006.12.116.

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28

Okazaki, Renji, Masaharu Ooka, Norihiro Tokitoh, and Naoki Inamoto. "Synthesis and reactions of 1,6-dithiocyanato- and 1,6-diiodo-1,3,5-cycloheptatrienes." Journal of Organic Chemistry 50, no. 2 (1985): 180–85. http://dx.doi.org/10.1021/jo00202a008.

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29

Coquerel, Yoann, and Jean-Pierre Deprés. "Reductive complexation of cycloheptatrienes by iron pentacarbonyl and catalytic sodium borohydride." Chemical Communications, no. 6 (February 27, 2002): 658–59. http://dx.doi.org/10.1039/b111618p.

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30

Solorio-Alvarado, César R., Yahui Wang, and Antonio M. Echavarren. "Cyclopropanation with Gold(I) Carbenes by Retro-Buchner Reaction from Cycloheptatrienes." Journal of the American Chemical Society 133, no. 31 (2011): 11952–55. http://dx.doi.org/10.1021/ja205046h.

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31

Platonov, Dmitry N., Aleksandr Yu Belyy, Ivan V. Ananyev, and Yury V. Tomilov. "Synthesis of 1,2,3,4,5,6,7-Heptasubstituted Cycloheptatrienes through Cycloaddition Reactions of Substituted Cyclopentadienones." European Journal of Organic Chemistry 2016, no. 23 (2016): 4105–10. http://dx.doi.org/10.1002/ejoc.201600516.

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32

Sugimura, Takashi, Naoko Ohuchi, Masami Kagawa, Kazutake Hagiya, and Tadashi Okuyama. "Regioselective Formation of Optically Active Cycloheptatrienes by Chiral Tethered Büchner Reaction." Chemistry Letters 33, no. 4 (2004): 404–5. http://dx.doi.org/10.1246/cl.2004.404.

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33

McGlinchey, Michael J. "Diels-Alder Additions as Mechanistic Probes–Interception of Silyl-Isoindenes: Organometallic Derivatives of Polyphenylated Cycloheptatrienes and Related Seven-Membered Rings." Molecules 25, no. 20 (2020): 4730. http://dx.doi.org/10.3390/molecules25204730.

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The intermediacy of short-lived isoindenes, generated in the course of metallotropic or silatropic shifts over the indene skeleton, can be shown by Diels-Alder trapping with tetracyanoethylene, leading to the complete elucidation of the dynamic behaviour of a series of polyindenylsilanes. Cyclopentadienones, bearing ferrocenyl and multiple phenyl or naphthyl substituents undergo [4 + 2] cycloadditions with diaryl acetylenes or triphenylcyclopropene to form the corresponding polyarylbenzenes or cycloheptatrienes. The heptaphenyltropylium cation, [C7Ph7+], was shown to adopt a nonplanar shallow

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34

Kilbas, Benan, and Metin Balci. "Palladium-catalyzed formation of oxazolidinones from biscarbamates: a mechanistic study." Beilstein Journal of Organic Chemistry 7 (February 24, 2011): 246–53. http://dx.doi.org/10.3762/bjoc.7.33.

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Oxazolidinones can be synthesized starting from cyclic biscarbamates via a palladium-catalyzed reaction. To test the proposed mechanism of this reaction, first, bicyclonorcarene endoperoxides derived from cyano and carbomethoxy cycloheptatrienes were synthesized and converted into the corresponding diols. The reaction of diols with toluenesulfonyl isocyanate followed by a palladium catalyzed reaction furnished oxazolidinone derivatives in similar yields. It was shown that, if one face of the double bond is blocked by substituents such as H or CN, the reaction also takes place. On the basis of

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35

Daub, Jörg, Adelheid Hasenhündl, Erika Salbeck, Alfred Gieren, and Thomas Hübner. "N,N,N′,N′,N′,N″,N‴,N‴-Octamethyl-[bi-2,4,6-cycloheptatrien-1-yl]- 3,3′-dicarboxamidinium-Salze: Struktur der meso-Verbindung in Lösung und im Kristall [1] / N,N,N′,N′,N′,N″,N‴,N‴-Octamethyl-[bi-2,4,6-cycloheptatriene-1-yl]- 3,3′-dicarboxamidinium Salts: Structure of the meso-Compound in Solution and in Solid State [1]." Zeitschrift für Naturforschung B 40, no. 10 (1985): 1390–97. http://dx.doi.org/10.1515/znb-1985-1025.

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3,3′-Bicycloheptatrienylamidinium salts 3 have been prepared by oxidative dimerization of 8 ,8 -bis(dimethylamino)heptafulvene (1). An X-ray structure analysis of the meso-octamethyl[bi-2,4,6-cycloheptatrienyl]3,3'-dicarboxamidinium-bis(triiodide) (3b) has been carried out. The dication 3 is centrosymmetric (Ci-symmetry) with boat shaped cycloheptatriene rings. The amidinium groups are twisted out of the plane of the C3(C3′)-C2(C2′) double bonds. The structure of the dication in the solid state is discussed in comparison with the structure in solution by aid of 1H NMR techniques. The N-methyls

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36

Solorio-Alvarado, César R., Yahui Wang, and A. M. Echavarren. "Correction to “Cyclopropanation with Gold(I) Carbenes by Retro-Buchner Reaction from Cycloheptatrienes”." Journal of the American Chemical Society 139, no. 6 (2017): 2529. http://dx.doi.org/10.1021/jacs.6b11935.

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37

Wang, Xi, Jianbo Wang, Zhikun Zhang, et al. "Synthesis of Trifluoromethylated Cycloheptatrienes from N-Tosylhydrazones: Transition-Metal-Free Büchner Ring Expansion." Synlett 26, no. 01 (2014): 59–62. http://dx.doi.org/10.1055/s-0034-1378937.

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38

Yin, Xiang, Giuseppe Zuccarello, Cristina García‐Morales, and Antonio M. Echavarren. "Gold(I)‐Catalyzed Intramolecular C(sp 3 )−H Insertion by Decarbenation of Cycloheptatrienes." Chemistry – A European Journal 25, no. 40 (2019): 9485–90. http://dx.doi.org/10.1002/chem.201900919.

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39

Solorio-Alvarado, Cesar R., Yahui Wang, and Antonio M. Echavarren. "ChemInform Abstract: Cyclopropanation with Gold(I) Carbenes by Retro-Buchner Reaction from Cycloheptatrienes." ChemInform 42, no. 52 (2011): no. http://dx.doi.org/10.1002/chin.201152047.

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40

Borrell, P. M., H. G. Löhmannsröben, and K. Luther. "Time Resolved Two-Color Multiphoton Ionization Studies on the Intramolecular Dynamics of Cycloheptatrienes." Berichte der Bunsengesellschaft für physikalische Chemie 89, no. 3 (1985): 274–75. http://dx.doi.org/10.1002/bbpc.19850890317.

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41

SENGUEL, M. E., Z. CEYLAN, and M. BALCI. "ChemInform Abstract: Unusual Triethylamine Catalyzed Rearrangement of Bicyclic Endoperoxides Derived from Substituted Cycloheptatrienes." ChemInform 28, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199748048.

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42

GREEN, M. L. H., P. MOUNTFORD, P. SCOTT, and V. S. B. MTETWA. "ChemInform Abstract: New Cycloheptatriene and Cycloheptatrienyl Derivatives of Niobium." ChemInform 22, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199123213.

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43

D'yakonov, Vladimir A., Gulnara N. Kadikova, Dmitry I. Kolokol'tsev, Ilfir R. Ramazanov та Usein M. Dzhemilev. "Titanium-Catalyzed [6π+2π]-Cycloaddition of Alkynes and Allenes to 7-Substituted 1,3,5-Cycloheptatrienes". European Journal of Organic Chemistry 2015, № 20 (2015): 4464–70. http://dx.doi.org/10.1002/ejoc.201500442.

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44

Yoshimura, Tomoyuki, Kanta Chino, and Jun-ichi Matsuo. "Concise synthesis of cycloheptatrienes from aldehydes and the Wittig reagent prepared from pyruvic ester." Tetrahedron Letters 73 (June 2021): 153150. http://dx.doi.org/10.1016/j.tetlet.2021.153150.

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45

Forst, Wendell, Guo-Ying Xu, and Grigorios Gidiotis. "Collisional energy transfer in non-reactive systems." Canadian Journal of Chemistry 65, no. 7 (1987): 1639–44. http://dx.doi.org/10.1139/v87-274.

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If the internal energy of target molecules highly dispersed in a heat bath is monitored as a function of time, their one-photon laser excitation and subsequent bulk collisional relaxation yields information only about energy transfer in the bulk system (a macroscopic time-dependent property). This paper discusses three special cases when [Formula: see text], the average energy transferred in a collision (a microscopic property) can be deduced from bulk relaxation data without knowledge of the collisional transition probability: (i) initial excitation is a δ function; (ii) relaxation of bulk av

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46

Menzek, Abdullah, and Metin Balcı. "Cycloaddition reactions of substituted cycloheptatrienes with benzyne and quinones: an entry to the substituted benzhomobarrelenes." Tetrahedron 49, no. 27 (1993): 6071–78. http://dx.doi.org/10.1016/s0040-4020(01)87191-x.

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47

Zhang, Zhikun, Jiajie Feng, Yan Xu, et al. "ChemInform Abstract: Synthesis of Trifluoromethylated Cycloheptatrienes from N-Tosylhydrazones: Transition-Metal-Free Buechner Ring Expansion." ChemInform 46, no. 22 (2015): no. http://dx.doi.org/10.1002/chin.201522075.

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48

Sprenger, Kristin, Christopher Golz, and Manuel Alcarazo. "Synthesis of Cycloheptatrienes, Oxepines, Thiepines, and Silepines: A Comparison between Brønsted Acid and Au‐Catalysis." European Journal of Organic Chemistry 2020, no. 39 (2020): 6245–54. http://dx.doi.org/10.1002/ejoc.202001072.

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49

Kuroda, Shigeyasu, Isao Hirano, Yanmei Zhang, Nguyen Chung Thanh, and Mitsunori Oda. "Synthesis, structure and some reactions of a multi-bridged unsaturated cyclooctadecane derivative formally having two cycloheptatrienes." Tetrahedron Letters 48, no. 33 (2007): 5811–15. http://dx.doi.org/10.1016/j.tetlet.2007.06.096.

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50

Dzhemilev, Usein M., Gulnara N. Kadikova, Dmitry I. Kolokol'tsev та Vladimir A. D'yakonov. "Catalytic [6π+2π]-cycloaddition of alkynes, 1,2- and 1,3-dienes to 1,3,5-cycloheptatrienes involving Ti complexes". Tetrahedron 69, № 23 (2013): 4609–11. http://dx.doi.org/10.1016/j.tet.2013.04.019.

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