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Journal articles on the topic 'Thermal rearrangements'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Zeller, Klaus-Peter. "Thermal Rearrangements of Azulenes." Bulletin des Sociétés Chimiques Belges 91, no. 5 (2010): 444. http://dx.doi.org/10.1002/bscb.198209105103.

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2

Jarzȩcki, Andrzej A., Joseph Gajewski, and Ernest R. Davidson. "Thermal Rearrangements of Norcaradiene." Journal of the American Chemical Society 121, no. 29 (1999): 6928–35. http://dx.doi.org/10.1021/ja984471l.

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3

Platz, M. S., Haiyong Huang, Francis Ford, and J. Toscano. "Photochemical rearrangements of diazirines and thermal rearrangements of carbenes." Pure and Applied Chemistry 69, no. 4 (1997): 803–8. http://dx.doi.org/10.1351/pac199769040803.

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4

KAWANO, Motoharu, and Katsutoshi TOMITA. "Thermal rearrangements for dioctahedral smectite." Journal of the Mineralogical Society of Japan 19 (1990): 11–15. http://dx.doi.org/10.2465/gkk1952.19.special_11.

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5

Casara, Patrick. "Vigabatrin synthesis by thermal rearrangements." Tetrahedron Letters 35, no. 19 (1994): 3049–50. http://dx.doi.org/10.1016/s0040-4039(00)76824-9.

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6

Billups, W. E., and Robert E. Bachman. "The thermal rearrangements of halocyclopropenes." Tetrahedron Letters 33, no. 14 (1992): 1825–26. http://dx.doi.org/10.1016/s0040-4039(00)74152-9.

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7

Wladislaw, B., L. Marzorati, and F. C. Biaggio. "Novel uncatalyzed thermal Pummerer rearrangements." Journal of Organic Chemistry 58, no. 22 (1993): 6132–34. http://dx.doi.org/10.1021/jo00074a051.

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8

Larsson, F. C. V., L. Brandsma, and S. O. Lawesson. "Thermal rearrangements of divinyl disulfides." Recueil des Travaux Chimiques des Pays-Bas 93, no. 9-10 (2010): 258–60. http://dx.doi.org/10.1002/recl.19740930908.

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9

Brown, R. F. C. "Thermal rearrangements of alkynes under FVP conditions. the acetylene-methylenecarbene rearrangement." Recueil des Travaux Chimiques des Pays-Bas 107, no. 12 (2010): 655–61. http://dx.doi.org/10.1002/recl.19881071202.

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10

Harrowven, David, Wei Sun, and Dharyl Wilson. "Steric Buttressing Changes Torquospecificity in Thermal Cyclobutenone Rearrangements, Providing New Opportunities for 5H-Furanone Synthesis." Synthesis 49, no. 14 (2017): 3091–106. http://dx.doi.org/10.1055/s-0036-1588850.

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Thermally induced rearrangements of 4-hydroxycyclobutenones are known to provide clean and reliable access to an array of useful carbocyclic and fused heterocyclic ring systems. Rarely, such reactions have been diverted to an alternative pathway leading to furanone formation. Herein, we show that these switches in the course of the rearrangement occur when a substrate bears a bulky substituent and are due to adverse steric buttressing as the transition state for electrocyclisation is approached. We also show how the reaction provides new opportunities for furanone synthesis and how bulky prot

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11

Baldwin, John E. "Thermal Rearrangements of Vinylcyclopropanes to Cyclopentenes." Chemical Reviews 103, no. 4 (2003): 1197–212. http://dx.doi.org/10.1021/cr010020z.

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12

Bui, Binh H., and Peter R. Schreiner. "Thermal Rearrangements of Heteroatom-Bridged Diallenes." European Journal of Organic Chemistry 2006, no. 18 (2006): 4187–92. http://dx.doi.org/10.1002/ejoc.200600270.

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13

Chen, Bin, and Anna K. Mapp. "Thermal and Catalyzed [3,3]-Phosphorimidate Rearrangements." Journal of the American Chemical Society 127, no. 18 (2005): 6712–18. http://dx.doi.org/10.1021/ja050759g.

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14

Stolle, Achim, Bernd Ondruschka, and Henning Hopf. "Thermal Rearrangements of Monoterpenes and Monoterpenoids." Helvetica Chimica Acta 92, no. 9 (2009): 1673–719. http://dx.doi.org/10.1002/hlca.200900041.

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15

Hopf, Henning, Dietmar Gottschild, and Winfried Lenk. "Thermal Rearrangements, XIII [1]. Thermal Isomerization of Exocyclic Allenes." Israel Journal of Chemistry 26, no. 2 (1985): 79–87. http://dx.doi.org/10.1002/ijch.198500074.

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16

Majumdar, K. C., G. H. Jana, S. K. Ghosh, and S. Saha. "Studies on sigmatropic rearrangements: Thermal rearrangement of 3-(meta-substituted aryloxymethyl) coumarins." Monatshefte f�r Chemie Chemical Monthly 128, no. 6-7 (1997): 641–50. http://dx.doi.org/10.1007/bf00807595.

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17

Carlsen, Per. "Thermal Rearrangement of 4Alkyl1,2,4triazoles. Rearrangements in the Crystalline State." Molecules 1, no. 10 (1997): 242–50. http://dx.doi.org/10.1007/s007830050043.

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18

Makhova, N. N., I. V. Ovchinnikov, A. S. Kulikov, S. I. Molotov, and E. L. Baryshnikova. "Monocyclic and cascade rearrangements of furoxans." Pure and Applied Chemistry 76, no. 9 (2004): 1691–703. http://dx.doi.org/10.1351/pac200476091691.

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Monocyclic rearrangements of azoles are extensively studied as alternative methods for the preparation of new heterocyclic systems. The present work is devoted to investigation of monocyclic and cascade rearrangements of 1,2,5-oxadiazole 2-oxide (furoxan) derivatives. It was found during investigations that rearrangements of furoxan ring had some peculiarities in comparison with analogous rearrangements of other azoles. Therefore, three different kinds of rearrangements were found. The first of them occurred through a dinitroso-ethylene intermediate and resulted in the synthesis of 1,2,3-triaz

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19

Hafner, Klaus, and Günter L. Knaup. "Thermal skeletal rearrangements of dimethyl 1,2-heptalenedicarboxylates." Tetrahedron Letters 27, no. 15 (1986): 1673–76. http://dx.doi.org/10.1016/s0040-4039(00)84344-0.

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20

Molander, Gary A., та Christopher T. Bibeau. "Thermal rearrangements of α-(ω-azidoalkyl) enones". Tetrahedron Letters 43, № 31 (2002): 5385–88. http://dx.doi.org/10.1016/s0040-4039(02)01077-8.

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21

Kroke, Edwin, Stefan Willms, Manfred Weidenbruch, Wolfgang Saak, Siegfried Pohl, and Heinrich Marsmann. "Siliranes: Formation, isonitrile insertions, and thermal rearrangements." Tetrahedron Letters 37, no. 21 (1996): 3675–78. http://dx.doi.org/10.1016/0040-4039(96)00650-8.

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22

Leber, Phyllis A., and John E. Baldwin. "Thermal [1,3] Carbon Sigmatropic Rearrangements of Vinylcyclobutanes." Accounts of Chemical Research 35, no. 5 (2002): 279–87. http://dx.doi.org/10.1021/ar010100p.

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23

Baldwin, John E., and Phyllis A. Leber. "Molecular rearrangements through thermal [1,3] carbon shifts." Org. Biomol. Chem. 6, no. 1 (2008): 36–47. http://dx.doi.org/10.1039/b711494j.

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24

De La Torre, Maria C., Pilar Fernandez, and Benjamin Rodriguez. "Thermal rearrangements of some neo-clerodane diterpenoids." Tetrahedron 43, no. 20 (1987): 4679–84. http://dx.doi.org/10.1016/s0040-4020(01)86910-6.

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25

Dulcere, Jean Pierre, Jack Crandall, Robert Faure, Maurice Santelli, Valerie Agati, and Mohamed N. Mihoubi. "Allenyl allylic ethers: synthesis and thermal rearrangements." Journal of Organic Chemistry 58, no. 21 (1993): 5702–8. http://dx.doi.org/10.1021/jo00073a032.

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26

Dolbier, William R., and Keith W. Palmer. "Thermal rearrangements of 9,10-bis(trifluorovinyl)phenanthrene." Journal of Organic Chemistry 58, no. 25 (1993): 7064–69. http://dx.doi.org/10.1021/jo00077a027.

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27

WLADISLAW, B., L. MARZORATI, and F. C. BIAGGIO. "ChemInform Abstract: Novel Uncatalyzed Thermal Pummerer Rearrangements." ChemInform 25, no. 9 (2010): no. http://dx.doi.org/10.1002/chin.199409079.

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28

CASARA, P. "ChemInform Abstract: Vigabatrin Synthesis by Thermal Rearrangements." ChemInform 25, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199437070.

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29

Kurita, Jyoji, Hiroichi Sakai, Sachiko Yamada, and Takashi Tsuchiya. "Novel thermal rearrangements of tetrahydrfo-azirinocyclobutabenzofuran derivatives." Journal of the Chemical Society, Chemical Communications, no. 4 (1987): 285. http://dx.doi.org/10.1039/c39870000285.

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30

BILLUPS, W. E., and R. E. BACHMAN. "ChemInform Abstract: The Thermal Rearrangements of Halocyclopropenes." ChemInform 23, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.199241061.

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31

CARLSEN, P., O. R. GAUTUN, and K. B. JORGENSEN. "ChemInform Abstract: Thermal Rearrangement of 4-Alkyl-1,2,4-triazoles. Rearrangements in the Crystalline State." ChemInform 28, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199737345.

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32

MAJUMDAR, K. C., G. H. JANA, S. K. GHOSH, and S. SAHA. "ChemInform Abstract: Studies on Sigmatropic Rearrangements: Thermal Rearrangement of 3-( meta-Substituted Aryloxymethyl) Coumarins." ChemInform 28, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.199741067.

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33

Bakardjiev, Mario, Josef Holub, Zdeňka Růžičková, et al. "Transformation of various multicenter bondings within bicapped-square antiprismatic motifs: Z-rearrangement." Dalton Transactions 50, no. 35 (2021): 12098–106. http://dx.doi.org/10.1039/d0dt04225k.

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Mutual rearrangements in the whole series of bicapped-square antiprismatic closo-C2B8H10 are reported. High-quality computations and experimentally observed thermal rearrangements disprove the earlier postulated dsd (diamond-square-diamond) scheme for these isomerizations.

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34

Price, John D., and Richard P. Johnson. "Thermal rearrangements of cyclic allenes retro-ene reactions." Tetrahedron Letters 26, no. 21 (1985): 2499–502. http://dx.doi.org/10.1016/s0040-4039(00)98820-8.

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35

Kjell, Douglas P., and Robert S. Sheridan. "A reinvestigation of the thermal rearrangements of naphthvalene." Tetrahedron Letters 26, no. 47 (1985): 5731–34. http://dx.doi.org/10.1016/s0040-4039(00)98910-x.

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36

Alker, David, Sivapathasuntharam Mageswaran, W. David Ollis, and Hooshang Shahriari-Zavareh. "Regiospecific thermal rearrangements of 2-allyloxypyridine N-oxides." Journal of the Chemical Society, Perkin Transactions 1, no. 6 (1990): 1631. http://dx.doi.org/10.1039/p19900001631.

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37

Baryshnikova, Ekaterina L., and Nina N. Makhova. "Thermal and base-induced rearrangements of furoxanylketones phenylhydrazones." Mendeleev Communications 10, no. 5 (2000): 190–91. http://dx.doi.org/10.1070/mc2000v010n05abeh001351.

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38

Billups, W. E., Rajesh K. Saini, Vladislav A. Litosh, Lawrence B. Alemany, William K. Wilson, and Kenneth B. Wiberg. "Thermal Rearrangements of Spiro[2.4]hepta-1,4,6-trienes." Journal of Organic Chemistry 67, no. 13 (2002): 4436–40. http://dx.doi.org/10.1021/jo011144e.

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39

Piers, Edward, Anderson Richard Maxwell, and Neil Moss. "Thermolysis of unsymmetrically substituted vinylcyclopropanes. Regarding the effect of oxygen substituents on the site-selectivity of homo-[1,5]-sigmatropic hydrogen migrations." Canadian Journal of Chemistry 63, no. 2 (1985): 555–57. http://dx.doi.org/10.1139/v85-090.

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Thermal rearrangement of compounds 1, 8–11, and 20 results, in each case, in the exclusive migration of the hydrogen (HΛ) not associated with the oxygen substituent. On the other hand, thermolysis of 19, 22, and 23 provides, in each case, a mixture of the two possible sigmatropic rearrangement products. Similar bond reorganization of the hydrocarbon 21 affords the dienes 27 and 28 (98:2, respectively). On the basis of these results, along with those reported earlier, it is proposed that in the transition states for these rearrangements (a) there is an accumulation of electron density at the ca

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40

Reichardt, Paul B., Barbara J. Anderson, Thomas P. Clausen, and L. Claron Hoskins. "Thermal instability of germacrone: implications for gas chromatographic analysis of thermally unstable analytes." Canadian Journal of Chemistry 67, no. 7 (1989): 1174–77. http://dx.doi.org/10.1139/v89-177.

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The rearrangement of germacrone (1) to β-elemenone (2) is common during gas chromatographic (GC) analysis, with the conversion taking place in the injector port at temperatures above 250 °C as well as on the column. While production of 2 in the injector is evident from the gas chromatographic trace, 2 produced from 1 during its migration down the column is difficult to detect because of the diffuse nature of the chromatographic peak produced by this process. A mathematical model and kinetic parameters (A = (1.35 ± 0.03) × 10−3s−1; Ea = 137 ± 4 kJ mol−1) determined from the reaction in solution

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41

Cariou, Kevin, Emily Mainetti, Louis Fensterbank, and Max Malacria. "Tandem PtCl2 catalyzed–thermal [3,3] rearrangements of enyne acetates." Tetrahedron 60, no. 43 (2004): 9745–55. http://dx.doi.org/10.1016/j.tet.2004.06.151.

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42

Scott, Lawrence T., Nicolas H. Roelofs, and Tsze Hong Tsang. "Thermal rearrangements of aromatic compounds. 10. Automerization of benzene." Journal of the American Chemical Society 109, no. 18 (1987): 5456–61. http://dx.doi.org/10.1021/ja00252a024.

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43

Likhotvorik, Igor R., Duncan W. Brown, and Maitland Jones. "Vinylidenes As Intermediates in Thermal Cyclopropene-to-Acetylene Rearrangements." Journal of the American Chemical Society 116, no. 14 (1994): 6175–78. http://dx.doi.org/10.1021/ja00093a016.

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44

Mizuno, Hideyuki, Hua Tong, Atsushi Ikeda, and Stefano Mossa. "Intermittent rearrangements accompanying thermal fluctuations distinguish glasses from crystals." Journal of Chemical Physics 153, no. 15 (2020): 154501. http://dx.doi.org/10.1063/5.0021228.

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45

Tiedemann, Ralf, Philip Turnbull, and Harold W. Moore. "Synthesis and Thermal Rearrangements of 4-Allyl-4-arylcyclobutenones." Journal of Organic Chemistry 64, no. 11 (1999): 4030–41. http://dx.doi.org/10.1021/jo990052a.

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46

Akhmedov, N. G., S. G. Malyugina, V. I. Mstislavsky, et al. "(Phenalene)chromium Tricarbonyl Complexes. Synthesis, Structure, and Thermal Rearrangements." Organometallics 17, no. 21 (1998): 4607–19. http://dx.doi.org/10.1021/om970781l.

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47

KROKE, E., S. WILLMS, M. WEIDENBRUCH, W. SAAK, S. POHL, and H. MARSMANN. "ChemInform Abstract: Siliranes: Formation, Isonitrile Insertions, and Thermal Rearrangements." ChemInform 27, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199638175.

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48

DOLBIER, W. R. JUN, and K. W. PALMER. "ChemInform Abstract: Thermal Rearrangements of 9,10-Bis(trifluorovinyl)phenanthrene." ChemInform 25, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.199416133.

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49

DULCERE, J. P., J. CRANDALL, R. FAURE, M. SANTELLI, V. AGATI, and M. N. MIHOUBI. "ChemInform Abstract: Allenyl Allylic Ethers: Synthesis and Thermal Rearrangements." ChemInform 25, no. 5 (2010): no. http://dx.doi.org/10.1002/chin.199405080.

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50

Leber, Phyllis A., and John E. Baldwin. "ChemInform Abstract: Thermal [1,3] Carbon Sigmatropic Rearrangements of Vinylcyclobutanes." ChemInform 33, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.200230292.

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