logo
CONTENT TYPES

Figure 1Loading Img

Conformational Analysis. III. Applications to Some Medium Ring Compounds1,2

Cite this: J. Am. Chem. Soc. 1959, 81, 21, 5727–5733
Publication Date (Print):November 1, 1959
https://doi.org/10.1021/ja01530a049
ACS Legacy Archive
Article Views
226
Altmetric
-
Citations
LEARN ABOUT THESE METRICS
PDF (859 KB)

Note: In lieu of an abstract, this is the article's first page.

Free first page

Cited By


This article is cited by 67 publications.

  1. Vladimir B. Orel, Anastasia A. Manzhueva. Thermodynamics and isomerism of products and intermediates of a one-pot superbase-promoted assembly of tetracyclic frontalin derivatives: A quantum chemical study. Journal of Molecular Structure 2020, 1215 , 128290. https://doi.org/10.1016/j.molstruc.2020.128290
  2. Pnina Dauber-Osguthorpe, A. T. Hagler. Biomolecular force fields: where have we been, where are we now, where do we need to go and how do we get there?. Journal of Computer-Aided Molecular Design 2019, 33 (2) , 133-203. https://doi.org/10.1007/s10822-018-0111-4
  3. A. T. Hagler. Force field development phase II: Relaxation of physics-based criteria… or inclusion of more rigorous physics into the representation of molecular energetics. Journal of Computer-Aided Molecular Design 2019, 33 (2) , 205-264. https://doi.org/10.1007/s10822-018-0134-x
  4. M.A.B. Larsen, A.B. Stephansen, T.I. Sølling. Coherent motion of excited state cyclic ketones: The have and the have-nots. Chemical Physics Letters 2017, 683 , 495-499. https://doi.org/10.1016/j.cplett.2017.04.030
  5. Valeri Poltev. Molecular Mechanics: Principles, History, and Current Status. 2017,,, 21-67. https://doi.org/10.1007/978-3-319-27282-5_9
  6. Salvatore Profeta. Molecular Modeling. 2016,,, 1-46. https://doi.org/10.1002/0471238961.1315120516181506.a01.pub3
  7. Valeri Poltev. Molecular Mechanics: Principles, History, and Current Status. 2015,,, 1-48. https://doi.org/10.1007/978-94-007-6169-8_9-2
  8. Jan Dillen. Conformational analysis of azepane, oxepane, silepane, phosphepane, thiepane and the azepanium cation by high level quantum mechanics. Structural Chemistry 2013, 24 (3) , 751-762. https://doi.org/10.1007/s11224-012-0192-y
  9. Carlos A. Stortz. Conformational pathways of simple six-membered rings. Journal of Physical Organic Chemistry 2010, 23 (12) , 1173-1186. https://doi.org/10.1002/poc.1689
  10. . Molecular Structures by Computational Methods. 2010,,, 28-50. https://doi.org/10.1002/9780470608852.ch3
  11. S. Das, E. R. Rani, M. K. Mahanti. Kinetics and mechanism of the oxidative cleavage of ketones by quinolinium dichromate. Kinetics and Catalysis 2007, 48 (3) , 381-389. https://doi.org/10.1134/S0023158407030068
  12. G. M. Kellie, F. G. Riddell. Non-Chair Conformations of Six-Membered Rings. 2007,,, 225-269. https://doi.org/10.1002/9780470147177.ch3
  13. Verónica García-Montalvo, M. Kenia Zamora-Rosete, Diego Gorostieta, Raymundo Cea-Olivares, R. Alfredo Toscano, Simón Hernández-Ortega. Organotellurium(IV) Derivatives of Tetraphenyldichalcogenoimidodiphosphinates − The Crystal and Molecular Structure of [C4H8TeI{Ph2(Se)PNP(Se)Ph2}], [C4H8TeI{Ph2(S)PNP(S)Ph2}], [C4H8Te{Ph2(S)PNP(S)Ph2}2], [C8H8TeI{Ph2(S)PNP(S)Ph2}], and [O(TeC4H8)2{Ph2(O)PNP(O)Ph2}]2[I, I3] Representing a Novel Type of Ring Systems. European Journal of Inorganic Chemistry 2001, 2001 (9) , 2279-2285. https://doi.org/10.1002/1099-0682(200109)2001:9<2279::AID-EJIC2279>3.0.CO;2-Y
  14. M. Fatima DaCruz, Marc Zimmer. Copper(II) six-membered rings: a molecular mechanics and cluster analysis. Inorganica Chimica Acta 1997, 261 (2) , 181-186. https://doi.org/10.1016/S0020-1693(97)05483-2
  15. Michael B. Bolger. Computational Techniques in Macromolecular Structural Analysis. 1995,,, 433-490. https://doi.org/10.1016/B978-012286230-4/50010-9
  16. J Eddie Baker. Limiting positions of a bricard linkage and their possible relevance to the cyclohexane molecule. Mechanism and Machine Theory 1986, 21 (3) , 253-260. https://doi.org/10.1016/0094-114X(86)90101-1
  17. Yoshinori Yamamoto, Hidetaka Yatagai, Yuji Ishihara, Norihiko Maeda, Kazuhiro Maruyama. Stereo- and regiocontrol of acyclic systems via the lewis acid mediated reaction of allylic stannanes with aldehydes. Tetrahedron 1984, 40 (12) , 2239-2246. https://doi.org/10.1016/0040-4020(84)80007-1
  18. Michael J. Cook, Ghoabad Ghaem-Maghami, Festus Kaberia, Knut Bergesen. 1H NMR spectra and conformational analysis of some 1,4-dithiepan-6-ones. Organic Magnetic Resonance 1983, 21 (5) , 339-343. https://doi.org/10.1002/omr.1270210511
  19. Johannes Leitich, Oskar E. Polansky, Werner Riemer, Ursula Ritter-Thomas. Zur Kenntnis organischerLewis-S�uren, 36.Cis?trans-Gleichgewichte und Konformationen von 2,(x)-Dialkyl-1-dicyanomethylencyclohexanen. Wahlweise einfache Darstellung dercis- odertrans-Formen. Monatshefte f�r Chemie Chemical Monthly 1982, 113 (4) , 485-494. https://doi.org/10.1007/BF00799924
  20. Peter W. Hickmott. Enamines: recent advances in synthetic, spectroscopic, mechanistic, and stereochemical aspects—I. Tetrahedron 1982, 38 (14) , 1975-2050. https://doi.org/10.1016/0040-4020(82)85149-1
  21. B. T. Ibragimov, S. A. Talipov, G. N. Tishchenko, Yu. K. Kushmuradov, T. F. Aripov, S. Kuchkarov. Molecular and crystal structure of tetrahydroneosophoramine. Chemistry of Natural Compounds 1981, 17 (6) , 546-551. https://doi.org/10.1007/BF00574374
  22. B. T. Ibragimov, S. A. Talipov, Yu. K. Kushmuradov, T. F. Aripov, S. Kuchkarov. Structure of lehmannine N-oxide. Chemistry of Natural Compounds 1981, 17 (6) , 552-557. https://doi.org/10.1007/BF00574375
  23. Kazuhiro Maruyama, Yuji Ishihara, Yoshinori Yamamoto. A short and stereoselective synthesis of the (±) Prelog-Djerassi lactonic acid. Tetrahedron Letters 1981, 22 (42) , 4235-4238. https://doi.org/10.1016/S0040-4039(01)82113-4
  24. S. -M. Nasirov, I. A. Israilov, L. G. Kuz'mina, M. S. Yunusov, Yu. T. Struchkov, S. Yu. Yunusov. X-ray structural investigation on alkaloids V. Crystal and molecular structure of sibiricine. Chemistry of Natural Compounds 1979, 14 (6) , 640-645. https://doi.org/10.1007/BF00937618
  25. D.A. Lightner, E.L. Docks. Analysis of cycloheptanone conformation from temperature dependent circular dichroism measurements of (+)-(3R)-methylcycloheptanone and (−)-(4R)-methylcycloheptanone. Tetrahedron 1979, 35 (5) , 713-720. https://doi.org/10.1016/0040-4020(79)87022-2
  26. S. -M. Nasirov, V. G. Andrianov, Yu. T. Struchkov, S. Yu. Yunusov. X-ray structural investigation of alkaloids. III. Molecular structure and absolute configuration of (+)-excelsine. Chemistry of Natural Compounds 1976, 12 (2) , 184-193. https://doi.org/10.1007/BF00566341
  27. Jacob V. Kainnady, Alfons Weber. High resolution Raman spectroscopy of gases with laser sources. IX. The rotational spectra of cycloheptane and cyclooctane. Journal of Raman Spectroscopy 1976, 4 (3) , 275-284. https://doi.org/10.1002/jrs.1250040309
  28. V. N. Krutii, S. A. Chelmakova, A. S. Gurovets, T. V. Vasina, D. B. Furman, V. Z. Sharf, A. L. Liberman. Conformation effects in reduction of methyl-substituted cyclopentanones with 2-propanol in presence of RhCl(PPh3)3 or RuCl2(PPh3)3. Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 1975, 24 (5) , 1019-1022. https://doi.org/10.1007/BF00922956
  29. A. L. Liberman, T. V. Vasina. Cycloketonization and linear polyketonization of ?, ?-dicarboxylic acids. Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 1975, 24 (4) , 771-775. https://doi.org/10.1007/BF00920691
  30. Y. Brunel, H. Faucher, D. Gagnaire, A. Rassat. Programme de minimisation de l'energie empirique d'une molecule par une methode simpliciale. Tetrahedron 1975, 31 (8) , 1075-1091. https://doi.org/10.1016/0040-4020(75)80129-3
  31. Naoji Matsumoto, Ju Kumanotani. C-13 NMR study on configurations of disubstituted cyclohexanone and cyclohexane derived therefrom by the Huang-Minlon process. Tetrahedron Letters 1975, 16 (42) , 3643-3646. https://doi.org/10.1016/S0040-4039(00)91346-7
  32. J�rg E. Heller, Andr� S. Dreiding. Konfigurationen und Konformationen von zwei 2,4,6,8-Tetrabrom-cyclooctan-1, 5-dionen. Helvetica Chimica Acta 1973, 56 (2) , 723-738. https://doi.org/10.1002/hlca.19730560217
  33. T. Srikrishnan, R. Srinivasan, R. Zand. Studies in molecular structure, symmetry and conformation I. Journal of Crystal and Molecular Structure 1971, 1 (3) , 199-212. https://doi.org/10.1007/BF01198532
  34. R. Srinivasan, T. Srikrishnan. Studies in molecular structure, symmetry and conformation—IV. Tetrahedron 1971, 27 (5) , 1009-1012. https://doi.org/10.1016/S0040-4020(01)92502-5
  35. Ariyuki Aihara, Chikazu Kitazawa. A Remark on the Dipole Moment of Cyclohexane-1,4-dione in Relation to Its Flexible Molecular Conformation. Bulletin of the Chemical Society of Japan 1971, 44 (1) , 99-103. https://doi.org/10.1246/bcsj.44.99
  36. I.O.C. Ekejiuba, H.E. Hallam. Infra-red and raman studies of conformational isomerism in cycloalkyl monohalides. Journal of Molecular Structure 1970, 6 (5) , 341-357. https://doi.org/10.1016/0022-2860(70)85001-3
  37. D. H. R. Barton. Die Prinzipien der Konformationsanalyse (Nobel-Vortrag). Angewandte Chemie 1970, 82 (20) , 827-834. https://doi.org/10.1002/ange.19700822003
  38. Philippe Desaulles, Jean-Pierre Fleury. Analyse Conformationnelle en Serie Alcoylidene-5 Dioxanne-1,3. Organic Magnetic Resonance 1970, 2 (3) , 245-249. https://doi.org/10.1002/mrc.1270020304
  39. B. A. Arbuzov, L. K. Yuldasheva, R. P. Arshinova. Conformation of benzylidenecyclohexanone, dibenzylidenecyclohexanone, and benzylidenecyclohexanone oxide. Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 1969, 18 (5) , 923-927. https://doi.org/10.1007/BF00922842
  40. Harold Booth. Chapter 3 Applications of 1H nuclear magnetic resonance spectroscopy to the conformational analysis of cyclic compounds. Progress in Nuclear Magnetic Resonance Spectroscopy 1969, 5 , 149-381. https://doi.org/10.1016/0079-6565(69)80013-0
  41. Bert Fraser-Reid, John T. Brewer, R. Li-jiun Sun. 4,6-dioxa-5-phenyl-2,8-dehydrocyclooctylidene: an indivertible carbene. Tetrahedron Letters 1969, 10 (32) , 2779-2782. https://doi.org/10.1016/S0040-4039(01)88267-8
  42. Hans Paulsen, Klaus Todt, Helmut Ripperger. Monosaccharide mit stickstoffhaltigem Ring, XVIII. Konformation und anomerer Effekt vonN-substituierten 2-Alkyl-piperidin-Derivaten. Chemische Berichte 1968, 101 (10) , 3365-3376. https://doi.org/10.1002/cber.19681011006
  43. N.L. Allinger, J.J. Maul. Conformational analysis—LXI. Tetrahedron 1968, 24 (11) , 4257-4266. https://doi.org/10.1016/0040-4020(68)88187-6
  44. W.T.de Kock, K.G.R. Pachler. Gafrinin, a sesquiternoid lactone from Geigeria africana gries-II. Tetrahedron 1968, 24 (4) , 1701-1705. https://doi.org/10.1016/S0040-4020(01)82476-5
  45. T.C. Joseph, Sukh Dev. Studies in sesquiterpenes—XXXI. Tetrahedron 1968, 24 (10) , 3841-3852. https://doi.org/10.1016/S0040-4020(01)92591-8
  46. A. Zschunke, F.-J. Strüber, R. Borsdorf. H1-NMR-spektren der alkylcycloheptanole. Tetrahedron 1968, 24 (12) , 4403-4410. https://doi.org/10.1016/S0040-4020(01)96279-9
  47. H. Paulsen, K. Todt. Cyclic Monosaccharides Having Nitrogen or Sulfur in the Ring. 1968,,, 115-232. https://doi.org/10.1016/S0096-5332(08)60169-1
  48. Michinori Oki, Hiizu Iwamura, Jun-ichi Aihara, Hiroshi Iida. Intramolecular Interaction between Hydroxyl Group and Carbonyl Moiety in Keto-alcohols. Bulletin of the Chemical Society of Japan 1968, 41 (1) , 176-182. https://doi.org/10.1246/bcsj.41.176
  49. G. A. Morrison. Conformational Analysis of Some Alkaloids. 1967,,, 269-317. https://doi.org/10.1007/978-3-7091-8164-5_9
  50. M. Bixon, S. Lifson. Potential functions and conformations in cycloalkanes. Tetrahedron 1967, 23 (2) , 769-784. https://doi.org/10.1016/0040-4020(67)85023-3
  51. J. Sicher, M. Svoboda, J. Závada, R.B. Turner, P. Goebel. Stereochemical studies—xxxvi. Tetrahedron 1966, 22 (2) , 659-671. https://doi.org/10.1016/0040-4020(66)80035-2
  52. T. Masamune, S. Ohuchi, S. Shimokowa, H. Booth. The condensed polynuclear perhydro-compounds containing nitrogen—XIV. Tetrahedron 1966, 22 (3) , 773-783. https://doi.org/10.1016/0040-4020(66)80048-0
  53. J. C. Celotti, L. Nagels, J. Reisse, G. Chiurdoglu. Étude Spectroscopique de Molécules Halogénées. IV. Analyse conformationnelle en série cyclooctanique. Bulletin des Sociétés Chimiques Belges 1965, 74 (1-2) , 62-70. https://doi.org/10.1002/bscb.19650740111
  54. J. Shabtai. Gas chromatography with stationary phases containing silver nitrate. Journal of Chromatography A 1965, 18 , 302-307. https://doi.org/10.1016/S0021-9673(01)80366-6
  55. Nelson J. Leonard, Andrew E. Yethon. New functional group combinations in medium rings. 3°-amine salt with sulfoxide. Tetrahedron Letters 1965, 6 (48) , 4259-4263. https://doi.org/10.1016/S0040-4039(00)71082-3
  56. Norman L. Allinger, Frederick M. Karkowski. The energy of the boat form of a simple cyclohexanone. Tetrahedron Letters 1965, 6 (26) , 2171-2174. https://doi.org/10.1016/S0040-4039(00)90173-4
  57. JOHN ARONSON, W. L. MEYER, T. D. BROCK. A Molecular Model for Chemical and Biological Differences between Streptomycin and Dihydrostreptomycin. Nature 1964, 202 (4932) , 555-557. https://doi.org/10.1038/202555a0
  58. L. M. Trefonas, Robert Towns. Crystal and molecular structure of 8,8-dimethyl-8-azoniabicyclo [5.1.0] octane iodide. Journal of Heterocyclic Chemistry 1964, 1 (1) , 19-22. https://doi.org/10.1002/jhet.5570010104
  59. Woldemar Schneider, Ruth Dillmann. Stickstoffhaltige Bicyclen, II. Synthesen in der 2-Aza-bicyclo[2.2.2]octan-Reihe. Chemische Berichte 1963, 96 (9) , 2377-2386. https://doi.org/10.1002/cber.19630960915
  60. Máximo Barón, O. Brieux De Mandirola, J. F. Westerkamp. THE STRUCTURE OF "METACHLORAL" (2,4,6,8-TETRAKIS-(TRICHLOROMETHYL)-1,3,5,7-TETROXACANE), A NEW CYCLIC TETRAMER OF CHLORAL. Canadian Journal of Chemistry 1963, 41 (8) , 1893-1897. https://doi.org/10.1139/v63-279
  61. M. Hanack. Methoden der Konformationsanalyse. Fresenius' Zeitschrift für analytische Chemie 1963, 197 (2) , 254-271. https://doi.org/10.1007/BF00468107
  62. Eugen Müller, Hans Huber. Photochemische Cyanierung, I Gesättigte Kohlenwasserstoffe. Chemische Berichte 1963, 96 (3) , 670-682. https://doi.org/10.1002/cber.19630960305
  63. W.D. Cotterill, M.J.T. Robinson. The origin of the reactivity of cyclohexanone. Tetrahedron Letters 1963, 4 (26) , 1833-1838. https://doi.org/10.1016/S0040-4039(01)90925-6
  64. M. Svoboda, M. Tichý, J. Fajkoš, J. Sicher. Chair-boat equilibria in fused cyclohexane systems. Tetrahedron Letters 1962, 3 (16) , 717-722. https://doi.org/10.1016/S0040-4039(00)70939-7
  65. Volker Franzen, Hans-Jürgen Schmidt. Zum Mechanismus der Hofmann-Eliminierung bei Sulfoniumsalzen, II. Chemische Berichte 1961, 94 (11) , 2937-2942. https://doi.org/10.1002/cber.19610941116
  66. D. H. R. Barton, G. A. Morrison. Conformational Analysis of Steroids and Related Natural Products. 1961,,, 165-241. https://doi.org/10.1007/978-3-7091-7156-1_4
  67. W. Klyne, V. Prelog. Description of steric relationships across single bonds. Experientia 1960, 16 (12) , 521-523. https://doi.org/10.1007/BF02158433

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE