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Journal articles on the topic 'Rearrangements (Chemistry) Carbinyl compounds'

Author: Grafiati

Published: 4 June 2021

Last updated: 8 February 2022

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1

Baldwin, John E., Samuel Bonacorsi, Robert G. Carlson, and Forest D. Graber. "Cyclohexyl(2-methylenecyclopropyl)carbinyl carbocationic rearrangements." Journal of Organic Chemistry 58, no. 4 (1993): 981–84. http://dx.doi.org/10.1021/jo00056a042.

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2

Tanko, James M., and Ray E. Drumright. "Radical ion probes. I. Cyclopropyl-carbinyl rearrangements of aryl cyclopropyl ketyl anions." Journal of the American Chemical Society 112, no. 13 (1990): 5362–63. http://dx.doi.org/10.1021/ja00169a060.

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3

Ranu, Brindaban C., Subhash Banerjee, and Arijit Das. "Catalysis by ionic liquids: cyclopropyl carbinyl rearrangements catalyzed by [pmim]Br under organic solvent free conditions." Tetrahedron Letters 47, no. 6 (2006): 881–84. http://dx.doi.org/10.1016/j.tetlet.2005.12.003.

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4

Vos, Johannes G., and Mary T. Pryce. "Photoinduced rearrangements in transition metal compounds." Coordination Chemistry Reviews 254, no. 21-22 (2010): 2519–32. http://dx.doi.org/10.1016/j.ccr.2010.04.010.

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5

Kolodiazhnyi, Oleg I., Evgen Grishkun, Oleg Golovatyi, and Sergei Ustenko. "Diastereoselective Rearrangements and Epimerization of Organophosphorus Compounds." Phosphorus, Sulfur, and Silicon and the Related Elements 109, no. 1-4 (1996): 485–88. http://dx.doi.org/10.1080/10426509608545196.

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6

Beck, Karin, Harald Burghard, Gabriele Fischer, Siegfried Hünig, and Petra Reinold. "Azo Cope Rearrangements of Nonstabilized Azo Compounds." Angewandte Chemie International Edition in English 26, no. 7 (1987): 672–73. http://dx.doi.org/10.1002/anie.198706721.

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7

Lerman, Berta M. "Skeletal rearrangements of cage compounds with medium rings." Russian Chemical Reviews 60, no. 4 (1991): 358–72. http://dx.doi.org/10.1070/rc1991v060n04abeh001082.

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8

Fañanás, Francisco J., Mónica Álvarez-Pérez, and Félix Rodríguez. "IPy2BF4-Mediated Rearrangements of 1,2-Difunctionalized Compounds and Olefins." Chemistry - A European Journal 11, no. 20 (2005): 5938–44. http://dx.doi.org/10.1002/chem.200500070.

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9

Magnusson, Göran. "REARRANGEMENTS OF EPOXY ALCOHOLS AND RELATED COMPOUNDS. A REVIEW." Organic Preparations and Procedures International 22, no. 5 (1990): 547–74. http://dx.doi.org/10.1080/00304949009356326.

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10

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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11

Downs, Jennifer R., Sally P. Grant, Jessica D. Townsend, et al. "Preparation of 4-anilino-6-aryl-2H-pyran-2-ones from trilithiated acetoacetanilides and aromatic esters." Canadian Journal of Chemistry 82, no. 5 (2004): 659–64. http://dx.doi.org/10.1139/v04-029.

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Acetoacetanilide and 4′-chloroacetoacetanilide were trilithiated with excess lithium diisopropylamide and condensed with several aromatic esters, followed by neutralization, separate acid cyclization, and rearrangements. After C-acylation of trilithiated acetoacetanilides and cyclization to 4H-pyran-4-ones, these compounds underwent multistep rearrangements to 4-anilino-6-aryl-2H-pyran-2-ones.Key words: pyranones, trianions, Claisen-type condensations, rearrangements.

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12

Atalla, A. A., A. M. Gaber, A. M. Kamal El-Dean, and Th A. Mohamed. "MOLECULAR REARRANGEMENTS OF SULPHUR COMPOUNDS (II)† PYROLYSIS OF SOME SUBSTITUTED THIAZOLIDINONES." Phosphorus, Sulfur, and Silicon and the Related Elements 57, no. 3-4 (1991): 255–60. http://dx.doi.org/10.1080/10426509108038857.

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13

Atalla, Ahemed A. "Molecular Rearrangements of Sulfur Compounds Thermolysis and Photolysis of Ketoxime Arenesulfonates." Phosphorus, Sulfur, and Silicon and the Related Elements 90, no. 1-4 (1994): 205–11. http://dx.doi.org/10.1080/10426509408016403.

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14

Cadierno, Victorio, Javier Francos та José Gimeno. "Microwave-assisted InCl3-catalyzed Meyer–Schuster rearrangement of propargylic aryl carbinols in aqueous media: a green approach to α,β-unsaturated carbonyl compounds". Tetrahedron Letters 50, № 33 (2009): 4773–76. http://dx.doi.org/10.1016/j.tetlet.2009.06.040.

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15

Hassner, Alfred, Simha Naidorf-Meir, Hugo E. Gottlieb, and Israel Goldberg. "Stereochemistry. 83. Unusual rearrangements in cage compounds due to proximity effects." Journal of Organic Chemistry 58, no. 21 (1993): 5699–701. http://dx.doi.org/10.1021/jo00073a031.

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16

Orpen, A. Guy, and Ian D. Salter. "Structural systematics. 2. Metal framework rearrangements in cluster compounds containing the Au2Ru3 fragment." Organometallics 10, no. 1 (1991): 111–17. http://dx.doi.org/10.1021/om00047a037.

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17

Moustafa, Moustafa S., Saleh M. Al-Mousawi, Hesham R. El-Seedi, and Mohamed H. Elnagdi. "Tales of the Unexpected in Synthesis of Polyfunctional Heteroaromatics." Current Organic Synthesis 15, no. 5 (2018): 587–602. http://dx.doi.org/10.2174/1570179414666171116152921.

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Background: Our research group has a longstanding interest in the synthesis of novel functionalized heteroaromatic compounds, and the development of new methods for this purpose. During our ongoing investigations, we recently had an instance to check the reproducibility of some published results concerning the chemistry of arylhydrazonals, enamines and other functionally substituted carbonyl compounds. This work has led to the discovery of some new rearrangements, and the revision of the structures originally assigned to several molecules. Objective: This review surveys some correction of seve

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18

Nowicki, Janusz. "Claisen, Cope and Related Rearrangements in the Synthesis of Flavour and Fragrance Compounds." Molecules 5, no. 12 (2000): 1033–50. http://dx.doi.org/10.3390/50801033.

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19

Grovenstein, Erling, Karla W. Black, Subhash C. Goel, et al. "Carbanions. 24. Rearrangements of (E)- and (Z)-2,2-diphenyl-3-pentenylalkali metal compounds." Journal of Organic Chemistry 54, no. 7 (1989): 1671–79. http://dx.doi.org/10.1021/jo00268a033.

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20

Gielen, M. "Organometallic Compounds. XIV. Representations of Intramolecular Rearrangements of Octahedral Complexes Via Digonal Twists." Bulletin des Sociétés Chimiques Belges 78, no. 7-8 (2010): 351–55. http://dx.doi.org/10.1002/bscb.19690780705.

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21

Ernouf, Guillaume, Jean-Louis Brayer, Christophe Meyer, and Janine Cossy. "Sigmatropic rearrangements of cyclopropenylcarbinol derivatives. Access to diversely substituted alkylidenecyclopropanes." Beilstein Journal of Organic Chemistry 15 (February 5, 2019): 333–50. http://dx.doi.org/10.3762/bjoc.15.29.

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Cyclopropenes constitute useful precursors of other classes of compounds incorporating a three-membered ring. Although the transformation of substituted cyclopropenes into alkylidenecyclopropanes can be accomplished through different strategies, this review is focusing specifically on the use of [2,3]- and [3,3]-sigmatropic rearrangements involving cyclopropenylcarbinol derivatives as substrates. These sigmatropic rearrangements, which have been developed in recent years, allow a remarkably efficient and stereoselective access to a wide variety of heterosubstituted and/or functionalized alkyli

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22

Badovskaya, L. A., та V. V. Poskonin. "Rearrangements and Tautomeric Transformations of Heterocyclic Compounds in Homogeneous Reaction Systems Furfural–Н2О2–Solvent". Russian Journal of General Chemistry 88, № 8 (2018): 1568–79. http://dx.doi.org/10.1134/s1070363218080030.

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23

Gielen, M., C. Depasse-Delit, and J. Nasielski. "Organometallic Compounds. XV Non Topological Representation of Intramolecular Rearrangements of Bipyramidal Five-Coordinate Complexes." Bulletin des Sociétés Chimiques Belges 78, no. 7-8 (2010): 357–58. http://dx.doi.org/10.1002/bscb.19690780706.

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24

Dudziński, Piotr, Wibke S. Husstedt, Andrej V. Matsnev, Joseph S. Thrasher, and Günter Haufe. "Synthesis and [3,3]-sigmatropic rearrangements of 5-(pentafluorosulfanyl)-pent-3-en-2-ol, its homologues, and trifluoromethyl analogues." Organic & Biomolecular Chemistry 19, no. 25 (2021): 5607–23. http://dx.doi.org/10.1039/d1ob00870f.

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[3,3]-Sigmatropic rearrangements based on different SF<sub>5</sub>-substituted allylic alcohols were investigated. The synthetic sequence developed for SF<sub>5</sub> compounds is also useful for CF<sub>3</sub> analogues and its application in Johnson–Claisen rearrangement.

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25

Boldyrev, A. I., and O. P. Charkin. "Nonrigid intramolecular rearrangements in AXk compounds with high coordination numbers (k=5, 6, and 7)." Journal of Structural Chemistry 25, no. 4 (1985): 599–622. http://dx.doi.org/10.1007/bf00747249.

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26

Polman, Jiří, та Alexander Kasal. "The synthesis of 5-methyl-19-nor-5β-pregna-9,16-diene-3,20-dione, 5-methyl-19-nor-5β-pregna-9,10-diene-3,6,20-trione and their analogues with annellated E ring". Collection of Czechoslovak Chemical Communications 56, № 12 (1991): 2892–905. http://dx.doi.org/10.1135/cccc19912892.

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The synthesis of compounds VII, XVII, XXXIV and XXXVII is described, in which biological activity is assumed. The key steps of their preparation are the dehalogenation of compound XVIII and radicalic deoxygenation of the 6β-hydroxy group in compound XXX, which take place without skeletal rearrangements.

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27

Vivona, Nicolò, Andrea Pace, Ivana Pibiri, and Silvestre Buscemi. "Molecular Rearrangements of 1-Oxa- 2-azoles as an Expedient Route to Fluorinated Heterocyclic Compounds." HETEROCYCLES 63, no. 11 (2004): 2627. http://dx.doi.org/10.3987/rev-04-584.

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28

Ferreira, Vitor F., Thais de B. da Silva, Fernanda P. Pauli, et al. "Dimroth´s Rearrangement as a Synthetic Strategy Towards New Heterocyclic Compounds." Current Organic Chemistry 24, no. 17 (2020): 1999–2018. http://dx.doi.org/10.2174/1385272824999200805114837.

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Molecular rearrangements are important tools to increase the molecular diversity of new bioactive compounds, especially in the class of heterocycles. This review deals specifically with a very famous and widely applicable rearrangement known as the Dimroth Rearrangement. Although it has originally been observed for 1,2,3-triazoles, its amplitude was greatly expanded to other heterocycles, as well as from laboratory to large scale production of drugs and intermediates. The reactions that were discussed in this review were selected with the aim of demonstrating the windows that may be open by th

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29

Meyer, H. J., J. Goldman, E. B. Pedersen, and S. O. Lawesson. "Studies on Organophosphorus Compounds XIV. HMPA-Induced rearrangements of N-Benzyl-carboxamides into 3-phenylpropionitriles." Bulletin des Sociétés Chimiques Belges 84, no. 7 (2010): 735–39. http://dx.doi.org/10.1002/bscb.19750840707.

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30

Eisch, John J., and Ramiro Sanchez. "Rearrangements of heterocyclic compounds. 5. The selective, oxophilic imination of ketones with bis(dichloroaluminum) phenylimide." Journal of Organic Chemistry 51, no. 10 (1986): 1848–52. http://dx.doi.org/10.1021/jo00360a036.

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31

Lygin, Alexander V., and Armin de Meijere. "Reactions ofortho-Lithiophenyl (-Hetaryl) Isocyanides with Carbonyl Compounds: Rearrangements of 2-Metalated 4H-3,1-Benzoxazines." Journal of Organic Chemistry 74, no. 12 (2009): 4554–59. http://dx.doi.org/10.1021/jo9004734.

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32

Minkin, V. I., A. G. Starikov, R. M. Minyaev, and A. A. Starikova. "Quantum-chemical modeling of metal coordination compounds with photoswitchable magnetic properties controlled by ligand rearrangements." Theoretical and Experimental Chemistry 46, no. 6 (2011): 363–70. http://dx.doi.org/10.1007/s11237-011-9167-0.

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33

Jankowski, Christopher K., André Pelletier, Eduardo Diaz T., et al. "On the origin of some cubebene derivatives — Diels–Alder adducts and the diene structures of solidago compounds." Canadian Journal of Chemistry 85, no. 11 (2007): 996–1005. http://dx.doi.org/10.1139/v07-112.

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Two reactions, HCl addition and the thermal and (or) microwave assisted Diels–Alder condensation, were performed on α-cubebene (1), a vinylcyclopropane-containing tricyclic sesquiterpene. The diene structures originating from these reactions and from subsequent rearrangements of 1 were identified. The stereochemistry of the resulting adducts was established using mostly 2D high-resolution NMR.Key words: cubebene, tricyclic terpenes from Solidago Canadensis L, Diels-Alder microwave condensation on vinylcyclopropane system.

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34

Kost, Daniel, Boris Gostevskii, and Inna Kalikhman. "Silicon rehybridization and molecular rearrangements in hypercoordinate silicon dichelates." Pure and Applied Chemistry 79, no. 6 (2007): 1125–34. http://dx.doi.org/10.1351/pac200779061125.

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Hydrazide-based hypercoordinate silicon dichelates are remarkably flexible in terms of geometry and reactivity: this paper demonstrates how rather subtle constitutional changes result in dramatic geometrical and reactivity changes. A change of ligand-donor group from NMe2 to N=CMe2 changes the solid-state geometry from bicapped tetrahedral to octahedral. These two geometries are shown to coexist in solution in dynamic equilibrium. Hexacoordinate complexes are shown to dissociate to pentacoordinate compounds in two distinct ways: ionic or neutral, depending on substitution. Hexacoordinate diche

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35

Bera, Mrinal K., Rimpa De, Antony Savarimuthu, et al. "DBU-Catalyzed Rearrangement of Secondary Propargylic Alcohols: An Efficient and Cost-Effective Route to Chalcone Derivatives." Synlett 31, no. 16 (2020): 1587–92. http://dx.doi.org/10.1055/s-0040-1707909.

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A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed rearrangement of diarylated secondary propargylic alcohols to give α,β-unsaturated carbonyl compounds has been developed. The typical 1,3-transposition of oxy functionality, characteristic of Mayer–Schuster rearrangements, is not observed in this case. A broad substrate scope, functional-group tolerance, operational simplicity, complete atom economy, and excellent yields are among the prominent features of the reaction. Additionally, the photophysical properties and crystal-structure-packing behavior of selected compounds were investigated a

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36

Debnath, Pradip. "Recent Advances in the Synthesis of Amides via Oxime Rearrangements and its Applications." Current Organic Synthesis 15, no. 5 (2018): 666–706. http://dx.doi.org/10.2174/1570179415666180416151039.

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Background: Amide bond formation reactions are the most important transformations in (bio)organic chemistry because of the widespread occurrence of amides in pharmaceuticals, natural products and biologically active compounds. The Beckmann rearrangement is a well-known method used for the preparation of secondary amides from ketoximes. But, most of the traditional protocols used for the Beckmann rearrangement create enormous amount of wastes. Thus, the atom economical synthesis of amides has got high priority among the chemists. However, under classical Beckmann conditions, aldoximes do not re

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37

Il'ichev, Yuri V. "Rearrangements of 2-Nitrobenzyl Compounds. 2. Substituent Effects on the Reactions of the Quinonoid Intermediates." Journal of Physical Chemistry A 107, no. 47 (2003): 10159–70. http://dx.doi.org/10.1021/jp0357121.

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38

Fletcher, James T., Matthew D. Hanson, Joseph A. Christensen, and Eric M. Villa. "Revisiting ring-degenerate rearrangements of 1-substituted-4-imino-1,2,3-triazoles." Beilstein Journal of Organic Chemistry 14 (August 10, 2018): 2098–105. http://dx.doi.org/10.3762/bjoc.14.184.

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The 1-substituted-4-imino-1,2,3-triazole motif is an established component of coordination compounds and bioactive molecules, but depending on the substituent identity, it can be inherently unstable due to Dimroth rearrangements. This study examined parameters governing the ring-degenerate rearrangement reactions of 1-substituted-4-imino-1,2,3-triazoles, expanding on trends first observed by L’abbé et al. The efficiency of condensation between 4-formyltriazole and amine reactants as well as the propensity of imine products towards rearrangement was each strongly influenced by the substituent i

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39

Maruoka, Keiji, Masaichi Hasegawa, Hisashi Yamamoto, Keisuke Suzuki, Masato Shimazaki, and Genichi Tsuchihashi. "Epoxy silyl ether rearrangements: a new, stereoselective approach to the synthesis of .beta.-hydroxy carbonyl compounds." Journal of the American Chemical Society 108, no. 13 (1986): 3827–29. http://dx.doi.org/10.1021/ja00273a046.

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40

Guan, Zong, Jan C. Namyslo, Martin H. H. Drafz, Martin Nieger, and Andreas Schmidt. "Dimerisation, rhodium complex formation and rearrangements of N-heterocyclic carbenes of indazoles." Beilstein Journal of Organic Chemistry 10 (April 10, 2014): 832–40. http://dx.doi.org/10.3762/bjoc.10.79.

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Deprotonation of indazolium salts at low temperatures gives N-heterocyclic carbenes of indazoles (indazol-3-ylidenes) which can be trapped as rhodium complexes (X-ray analysis). In the absence of Rh, the indazol-3-ylidenes spontaneously dimerize under ring cleavage of one of the N,N-bonds and ring closure to an indazole–indole spiro compound which possesses an exocyclic imine group. The E/Z isomers of the imines can be separated by column chromatography when methanol is used as eluent. We present results of a single crystal X-ray analysis of one of the E-isomers, which equilibrate in solution

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41

Bleckmann, P., U. Englich, U. Hermann, et al. "Synthesis and Reactivity of Novel Bis(stannyl)silanes." Zeitschrift für Naturforschung B 54, no. 9 (1999): 1188–96. http://dx.doi.org/10.1515/znb-1999-0916.

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Bis(stannyl)silanes of types R3Sn-SiR′2-SnR3 and R2(H)Sn-SiR′2-Sn(H)R2 with R′ being methyl, phenyl, iso-propyl or terf-butyl have been synthesized by treatment of difunctionalized diorganosilanes with alkali stannides (R = Me, tBu; R′= Me, iPr; 1 - 6, 8 ) or with triphenyltin chloride and magnesium (R = Ph; R′ = Me, iPh;Pr; 7, 9). Me3Sn-SitBu2-SnMe3 4, was halogenated using SnCl4, to yield the bis(chlorostannyl)silane 11. The reaction of bis(stannyl)diorganosilanes R3SnSiR′SnR3 with catalytic amounts of Pd(PPh3)4 resulted in unexpected rearrangements under formation of the silyldistannanes R3

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42

Fajkoš, Jan, та Jiří Joska. "Solvolytic rearrangements in 4β,5-cyclopropano-5β-androstane-3β,17β,19-triol 3-acetate 17-benzoate 19-p-toluenesulfonate". Collection of Czechoslovak Chemical Communications 54, № 3 (1989): 751–59. http://dx.doi.org/10.1135/cccc19890751.

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The title tosylate V was prepared from the tosylate III by Simmons-Smith methylenation. Its acetolysis afforded three products with modified steroid skeletons: The diene VIII, the olefin XI, and the pentacyclic diacetate XIII. The 3-oxo derivatives XIV, XVI, XVII, and XIX-compounds of potentional biological interest-were prepared as follows: Oxidation of the monoacetate X followed by hydrolysis yielded the testosterone analogue XIV and oxidation of the diol IX gave the dione XVI. Using similar reaction sequence the triol diester XII afforded the oxo compounds XVII and XIX.

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43

Taran, Martine, and Bernard Delmond. "Obtention de nouveaux squelettes diterpéniques lors de l'isomérisation d'époxydes diterpéniques sur alumine active." Canadian Journal of Chemistry 66, no. 7 (1988): 1558–65. http://dx.doi.org/10.1139/v88-253.

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The isomerization of diterpene epoxides on active neutral alumina has established the existence of new rearrangements of the diterpene skeleton. Methyl 8,14β-epoxysandarcopimarate leads to bicyclic diterpene compounds by a Grob fragmentation, to derivatives of cleistanthane by a 1,2 migration of the vinyl substituent, as well as to one cycloditerpene compound. The 7,8 (or 8,9) derivatives of methyl isopimarate lead essentially to hydroxyolefins formed by a bifunctional acid–base mechanism at the alumina surface. [Journal translation]

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44

Reissig, Hans-Ulrich, Gesine Böttcher, and Reinhold Zimmer. "New 1,3-dihydroazepin-2-one derivatives by [3,3]-sigmatropic rearrangement of suitably substituted 2-alkenylcyclopropyl isocyanates." Canadian Journal of Chemistry 82, no. 2 (2004): 166–76. http://dx.doi.org/10.1139/v03-186.

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The 2-siloxysubstituted 2-alkenylcyclopropanecarboxylic acids 1014 were converted into the corresponding carbonyl azides by treatment with DPPA (diphenyl phosphorazidate) and triethylamine. On heating to 80 °C these intermediates smoothly furnished azepinone derivatives 1925 in moderate to good overall yields, which are the result of a sequence of Curtius reaction to cyclopropylisocyanates, [3,3]-sigmatropic rearrangement, and a final proton shift. The primary products may undergo desilylation (to afford azepin-2,5-diones such as 23) or double bond migration (to compound 25). Cyclopropanecar

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45

Mihova, Tonya R., Latchezar S. Trifonov, Valentin S. Dimitrov, Alexander S. Orahovats, Anthony Linden, and Heinz Heimgartner. "New Polycyclic Compounds from Photochemical Rearrangements of Some Substituted 2-Azatricyclo[5.2.2.01,5]undeca-4,8,10-trien-3-ones." Helvetica Chimica Acta 74, no. 5 (1991): 1011–26. http://dx.doi.org/10.1002/hlca.19910740512.

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46

Enriquez, F., F. J. López-Herrera, J. J. Quirante та F. Sarabia. "AM1 study of Wolff and 1,2-hydrogen shift rearrangements of β-oxy-α-Diazo carbonyl compounds". Theoretica Chimica Acta 94, № 1 (1996): 13–22. http://dx.doi.org/10.1007/bf00190152.

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47

Scott, Lawrence T., Mohammed M. Hashemi, Thomas H. Schultz, and Michael B. Wallace. "Thermal rearrangements of aromatic compounds. 15. Automerization of naphthalene. New evidence consistent with the intermediacy of benzofulvene." Journal of the American Chemical Society 113, no. 25 (1991): 9692–93. http://dx.doi.org/10.1021/ja00025a055.

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48

Calad, Stacie A., and K. A. Woerpel. "Silylene Transfer to Carbonyl Compounds and Subsequent Ireland−Claisen Rearrangements to Control Formation of Quaternary Carbon Stereocenters." Journal of the American Chemical Society 127, no. 7 (2005): 2046–47. http://dx.doi.org/10.1021/ja042893r.

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49

Yates, Peter, and Magdy Kaldas. "Rearrangements in the acid-catalyzed formation of lactones from 2-hydroxynorbornane-2-acetic acid derivatives and related compounds." Canadian Journal of Chemistry 70, no. 9 (1992): 2491–501. http://dx.doi.org/10.1139/v92-315.

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A mixture of the epimeric ethyl 2-hydroxynorbornane-2-acetates (1) on treatment with concentrated sulfuric acid is converted in turn to the lactones of exo-2-hydroxynorbornane-1-acetic acid (4), endo-6-hydroxynorbornane-endo-2-acetic acid (5), and exo-3-hydroxynorbornane-exo-2-acetic acid (6). With trifluoroacetic acid or 50% sulfuric acid, 1 gives 4, but this does not react further. In concentrated sulfuric acid the parent acids of 1 (7) and (E)- and (Z)-(norborn-2-ylidene)acetic acids (8 and 9) and their ethyl esters (10 and 11) give 6 as the infinity product. A mixture of 5-norbornene-endo-

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Janzen, Alexander F., and Meehae Jang. "Isomerization, fluorine exchange, and stereoselective synthesis of cis- and trans-F2TePh3Cl: application of the coordination model of reaction mechanisms." Canadian Journal of Chemistry 67, no. 1 (1989): 71–75. http://dx.doi.org/10.1139/v89-012.

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Abstract:

The stereoselective synthesis of cis- and trans-F2TePh3Cl (phenyl substituents adopt a mer arrangement) via 5-coordinate cations Ph3TeFCl+ and [Formula: see text] is described. trans-F2TcPh3Cl isomerizes to the thermodynamically more stable cis isomer, and cis -F2TePh3Cl has non-equivalent fluorines which undergo stereoselective fluorine exchange, as confirmed by 19F and l25Te nmr spectroscopy. These results are consistent with an intermolecular mechanism of isomerization and fluorine exchange involving Te—F bond cleavage.The coordination model of reaction mechanisms provides a unified descrip

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