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Cycloadditions of cyclic allyl cations to furan. Configuration and conformational analysis of the resulting bridged six-membered rings. Isolation and identification of boat and chair atropisomers

Cite this: J. Am. Chem. Soc. 1974, 96, 17, 5466–5478
Publication Date (Print):August 1, 1974
https://doi.org/10.1021/ja00824a025
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This article is cited by 30 publications.

  1. Ian W. Jones,, Yasunari Monguchi,, Alice Dawson,, Michael D. Carducci, and, Eugene A. Mash. Synthesis of 1,10-Dimethylbicyclo[8.8.8]hexacosane and 1,10-Dihydroxybicyclo[8.8.8]hexacosane. Organic Letters 2005, 7 (14) , 2841-2843. https://doi.org/10.1021/ol050714k
  2. Michael Harmata,, Saleh Elomari, and, Charles L. Barnes. Intramolecular 4 + 3 Cycloadditions. Cycloaddition Reactions of Cyclic Alkoxyallylic and Oxyallylic Cations. Journal of the American Chemical Society 1996, 118 (12) , 2860-2871. https://doi.org/10.1021/ja952740r
  3. Paolo Disetti, Linda Piras, Maria Moccia, Michele Saviano, Mauro F. A. Adamo. Model Studies for the Preparation of Oxepanes and Fused Compounds by Tandem [4+3] Cycloaddition/Ring-Opening Metathesis/Cross Metathesis. European Journal of Organic Chemistry 2017, 2017 (41) , 6202-6208. https://doi.org/10.1002/ejoc.201700994
  4. Paul Knochel, Paul Knochel, Nathalie Grenouillat, Vikas Sikervar. Zinc. 2017,,, 1-18. https://doi.org/10.1002/047084289X.rz001.pub3
  5. . References. 2010,,, 587-673. https://doi.org/10.1002/9783527632220.refs
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  7. Paul Knochel, Paul Knochel, Nathalie Grenouillat. Zinc. 2006,,https://doi.org/10.1002/047084289X.rz001.pub2
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  10. James H. Rigby, F. Christopher Pigge. [4 + 3] Cycloaddition Reactions. 1997,,, 351-478. https://doi.org/10.1002/0471264180.or051.03
  11. Michael Harmata. Intramolecular cycloaddition reactions of allylic cations. Tetrahedron 1997, 53 (18) , 6235-6280. https://doi.org/10.1016/S0040-4020(97)00051-3
  12. Michael Harmata. Intramolecular [4+3] cycloaddition reactions. 1997,,, 41-86. https://doi.org/10.1016/S1052-2077(97)80004-2
  13. JM Goodman, HMR Hoffmann, JG Vinter. On the configuration and conformation of oxyallyls in medium and large rings. Tetrahedron Letters 1995, 36 (42) , 7757-7760. https://doi.org/10.1016/0040-4039(95)01618-R
  14. Michael Harmata, Saleh Elahmad, Charles L. Barnes. Intramolecular4+3cycloadditions. Model studies toward the synthesis of ingenanes. Tetrahedron Letters 1995, 36 (9) , 1397-1400. https://doi.org/10.1016/0040-4039(95)00009-2
  15. Ingo Stohrer, H. Martin R. Hoffmann. Highly Diastereoselective Aldol Reaction of Bicyclo[3.2.1]oct-6-en-3-ones and 8-Oxabicyclo[3.2.1]oct-6-en-3-ones. (E)-Selective conversion into ?-alkylidene ketones. Helvetica Chimica Acta 1993, 76 (6) , 2194-2209. https://doi.org/10.1002/hlca.19930760604
  16. Ingo Stohrer, H.Martin R. Hoffmann. Synthesis of nonenolizable 6-hydroxy-2,4-cycloheptadien-1-ones. Tetrahedron 1992, 48 (29) , 6021-6032. https://doi.org/10.1016/S0040-4020(01)89850-1
  17. Navalkishore N. Joshi, H. Martin, R. Hoffmann. Ultrasonics in the metal promoted cycloaddition of α,α′-dibromo ketones to 1,3-dienes. Tetrahedron Letters 1986, 27 (6) , 687-690. https://doi.org/10.1016/S0040-4039(00)84073-3
  18. H. M. R. Hoffmann. Die Cycloaddition von Allyl-Kationen an 1,3-Diene: Eine allgemeine Methode zur Synthese siebengliedriger Carbocyclen. Angewandte Chemie 1984, 96 (1) , 29-48. https://doi.org/10.1002/ange.19840960106
  19. James D. White. Methynolide and the Prelog–Djerassi Lactonic Acid: An Exercise in Stereocontrolled Synthesis. 1984,,, 347-366. https://doi.org/10.1016/B978-0-12-450280-2.50017-X
  20. M.V. Sargent, F.M. Dean. Furans and their Benzo Derivatives: (ii) Reactivity. 1984,,, 599-656. https://doi.org/10.1016/B978-008096519-2.00061-8
  21. . Volume 4 References. 1984,,, 1085-1195. https://doi.org/10.1016/B978-008096519-2.00132-6
  22. Baldur Föhlisch, Rolf Herter, Elisabeth Wolf, John J. Stezowski, Emil Eckle. Synthese von 3-Oxo-8-oxabicyclo[3.2.1]oct-6-en-2-carbonitrilen aus γ-Brom-β-oxonitrilen und Furan via [4 + 3]-Cycloaddition von 1-Cyanallylium-2-olaten. Chemische Berichte 1982, 115 (1) , 355-380. https://doi.org/10.1002/cber.19821150132
  23. Baldur Föhlisch, Wolfgang Gottstein, Roland Kaiser, Iris Wanner. Erzeugung und cycloaddition von allyliumionen aus α-halogenketonen unter solvolyse-bedingungen. Tetrahedron Letters 1980, 21 (31) , 3005-3008. https://doi.org/10.1016/0040-4039(80)88022-1
  24. Peter Matzinger, Conrad Hans Eugster. Favorskii-Umlagerung in Gegenwart von 3,4-Dimethoxyfuran: 11endo-oxa-tricyclo [4.3.1.12,5]undec-3-en-10-on und Derivate. Helvetica Chimica Acta 1979, 62 (7) , 2325-2328. https://doi.org/10.1002/hlca.19790620728
  25. Paul G. Gassman, Stewart R. Korn, Thomas F. Bailey, Thomas H. Johnson, Janet Finer, Jon Clardy. The synthesis and structure of 10,11-bistrifluoromethyl-i,o-bicyclo[7.2.2]trideca-10,12-diene. A highly strained inside-outside bicycloalkane derivative.. Tetrahedron Letters 1979, 20 (36) , 3401-3404. https://doi.org/10.1016/S0040-4039(01)95420-6
  26. Francis A. Carey, Richard J. Sundberg. Conformational and Other Steric Effects. 1977,,, 71-123. https://doi.org/10.1007/978-1-4615-8882-5_3
  27. Raymond A. Firestone. The diradical mechanism for 1,3-dipolar cycloadditions and related thermal pericyclic reactions. Tetrahedron 1977, 33 (23) , 3009-3039. https://doi.org/10.1016/0040-4020(77)80448-1
  28. Richard J. Sundberg, Richard L. Parton. Ground State Conformational Control of Stereochemistry of a Photochemical Synthesis of the Quebrachamine-Dihydrocleavamine Skeleton. Tetrahedron Letters 1976, 17 (15) , 1163-1166. https://doi.org/10.1016/S0040-4039(00)78007-5
  29. H.M.R. Hoffmann, M.N. Iqbal. Improved procedure for the generation of allyl cations from simple dibromo ketones. Change of mechanism on reaction with triethyl borate amd zinc. Cycloadditions to conjugated dienes.. Tetrahedron Letters 1975, 16 (50) , 4487-4490. https://doi.org/10.1016/S0040-4039(00)91100-6
  30. J. G. VINTER, H. M. R. HOFFMANN. ChemInform Abstract: CYCLOADDITIONS OF CYCLIC ALLYLIC CATIONS TO FURAN, CONFIGURATION AND CONFORMATIONAL ANALYSIS OF THE RESULTING BRIDGED SIX-MEMBERED RINGS, ISOLATION AND IDENTIFICATION OF BOAT AND CHAIR ATROPISOMERS. Chemischer Informationsdienst 1974, 5 (44) , no-no. https://doi.org/10.1002/chin.197444237

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