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Axial-equatorial stability reversal in all-trans-polyalkylcyclohexanes

Cite this: J. Am. Chem. Soc. 1990, 112, 25, 9300–9307
Publication Date (Print):December 1, 1990
https://doi.org/10.1021/ja00181a036
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This article is cited by 22 publications.

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  2. David G. Hilmey,, Barry D. Davis,, Judith C. Gallucci,, Jennifer S. Brodbelt, and, Leo A. Paquette. X-ray Crystallographic and Mass Spectrometric Probing of the Conformational and Ionophoric Properties of Stereoisomeric Hexatetrahydrofuranylhexane Segments. The Journal of Organic Chemistry 2007, 72 (24) , 9088-9101. https://doi.org/10.1021/jo7016229
  3. Q. Shen and, M. Traetteberg. Molecular Structure of 2,2,4,4,6,6-Hexamethyl-1,3,5-trimethylenecyclohexane As Determined by Gas-Phase Electron Diffraction. The Journal of Organic Chemistry 2004, 69 (6) , 2094-2098. https://doi.org/10.1021/jo0303259
  4. Jörg Weiser,, Oren Golan,, Lutz Fitjer, and, Silvio E. Biali. Chair/Twist-Boat Energy Gap in Monocyclic, Conformationally Unconstrained Polyalkylcyclohexanes. The Journal of Organic Chemistry 1996, 61 (23) , 8277-8284. https://doi.org/10.1021/jo961526y
  5. Leo A. Paquette,, Marshall Stepanian,, Bruce M. Branan,, Scott D. Edmondson,, Cary B. Bauer, and, Robin D. Rogers. Conformational Analysis of Poly(spirotetrahydrofuranyl)cyclohexyl Systems. The Preference of Multiple C−O Bonds for Equatorial Occupancy. Journal of the American Chemical Society 1996, 118 (18) , 4504-4505. https://doi.org/10.1021/ja953972t
  6. Ishay Columbus,, Roy E. Hoffman, and, Silvio E. Biali. Stereochemistry and Conformational Anomalies of 1,2,3- and 1,2,3,4-Polycyclohexylcyclohexanes. Journal of the American Chemical Society 1996, 118 (29) , 6890-6896. https://doi.org/10.1021/ja960380h
  7. Maša Podunavac, Artur K. Mailyan, Jeffrey J. Jackson, Alenka Lovy, Paula Farias, Hernan Huerta, Jordi Molgó, Cesar Cardenas, Armen Zakarian. Scalable Total Synthesis, IP3R Inhibitory Activity of Desmethylxestospongin B, and Effect on Mitochondrial Function and Cancer Cell Survival. Angewandte Chemie 2021, https://doi.org/10.1002/ange.202102259
  8. Maša Podunavac, Artur K. Mailyan, Jeffrey J. Jackson, Alenka Lovy, Paula Farias, Hernan Huerta, Jordi Molgó, Cesar Cardenas, Armen Zakarian. Scalable Total Synthesis, IP3R Inhibitory Activity of Desmethylxestospongin B, and Effect on Mitochondrial Function and Cancer Cell Survival. Angewandte Chemie International Edition 2021, https://doi.org/10.1002/anie.202102259
  9. Fernando Rodríguez, Víctor J. Somovilla, Francisco Corzana, Jesús H. Busto, Alberto Avenoza, Prof Jesús M. Peregrina. Cyclohexane Ring as a Tool to Select the Presentation of the Carbohydrate Moiety in Glycosyl Amino Acids. Chemistry – A European Journal 2012, 18 (16) , 5096-5104. https://doi.org/10.1002/chem.201103089
  10. Magdaline Koutsaplis, Philip C. Andrews, Steven D. Bull, Peter J. Duggan, Benjamin H. Fraser, Paul Jensen. A new diastereoselective aza-allyl conjugate addition–Michael addition–ring closure reaction sequence and its application in the construction of six contiguous stereogenic centres. Chemical Communications 2007, 44 (34) , 3580. https://doi.org/10.1039/b707707f
  11. Kotaro Okajima, Tatsuya Mukae, Hiroshi Imagawa, Yoshiaki Kawamura, Mugio Nishizawa, Hidetoshi Yamada. Achievement of ring inversion of myo-inositol derivatives due to silyloxy/silyloxy repulsion enhanced by the trans-substituents on both sides. Tetrahedron 2005, 61 (14) , 3497-3506. https://doi.org/10.1016/j.tet.2005.01.124
  12. Hidetoshi Yamada, Kotaro Okajima, Hiroshi Imagawa, Tatsuya Mukae, Yoshiaki Kawamura, Mugio Nishizawa. Stable axial-rich chair conformer of myo-inositol derivatives due to introduction of two adjacent bulky silyl protections. Tetrahedron Letters 2004, 45 (15) , 3157-3160. https://doi.org/10.1016/j.tetlet.2004.02.080
  13. Samuel Siegel. Rhodium on Alumina. 2001,,https://doi.org/10.1002/047084289X.rr003
  14. Adriana M Namba, Salvador León, Gil Valdo José da Silva, Carlos Alemán. Dynamics of p-Menthan-3,9-diols. A Computational Study in Aqueous and Chloroform Solutions of Two Epimers. Tetrahedron 2000, 56 (33) , 6089-6097. https://doi.org/10.1016/S0040-4020(00)00558-5
  15. Reinhard W. Hoffmann. Konformationsdesign offenkettiger Verbindungen. Angewandte Chemie 2000, 112 (12) , 2134-2150. https://doi.org/10.1002/1521-3757(20000616)112:12<2134::AID-ANGE2134>3.0.CO;2-V
  16. Ishay Columbus, Manal Haj-Zaroubi, Jay S. Siegel, Silvio E. Biali. Face Selectivity in the Hydrogenation of Calixarene Ethers. The Journal of Organic Chemistry 1998, 63 (25) , 9148-9149. https://doi.org/10.1021/jo981551z
  17. Ishay Columbus, Silvio E. Biali. Stereochemistry of polycyclohexyl systems. Chirality 1998, 10 (1-2) , 159-168. https://doi.org/10.1002/chir.25
  18. Ishay Columbus, Shmuel Cohen, Silvio E. Biali. Cis-trans-trans-1,2,3,4-Tetracyclohexylcyclohexane: a Monocyclic Unconstrained Cyclohexane Existing in a Twist-Boat Conformation. 1995,,, 179-183. https://doi.org/10.1007/978-94-011-0353-4_21
  19. Rainer Stürmer, Reinhard W. Hoffmann. Stereoselective Synthesis of Alcohols, XLVIII[1] Linear Synthesis of (9S)-Dihydro-Erythronolide A. Chemische Berichte 1994, 127 (12) , 2519-2526. https://doi.org/10.1002/cber.19941271225
  20. Reinhard W. Hoffmann. Flexible Moleküle mit definierter Gestalt — Konformationsdesign. Angewandte Chemie 1992, 104 (9) , 1147-1157. https://doi.org/10.1002/ange.19921040905
  21. Reinhard W. Hoffmann. Flexible Molecules with Defined Shape?Conformational Design. Angewandte Chemie International Edition in English 1992, 31 (9) , 1124-1134. https://doi.org/10.1002/anie.199211241
  22. O. GOLAN, Z. GOREN, S. E. BIALI. ChemInform Abstract: Axial/Equatorial Stability Reversal in all-trans-Polyalkylcyclohexanes.. ChemInform 1991, 22 (12) , no-no. https://doi.org/10.1002/chin.199112150

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