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Unusually facile bridgehead enolization. Locked boat forms in anti-Bredt olefins

Cite this: J. Am. Chem. Soc. 1975, 97, 4, 904–905
Publication Date (Print):February 1, 1975
https://doi.org/10.1021/ja00837a043
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This article is cited by 12 publications.

  1. Gerard M. P. Giblin,, Douglas T. Kirk,, Lee Mitchell, and, Nigel S. Simpkins. Bridgehead Enolates:  Substitution and Asymmetric Desymmetrization of Small Bridged Carbonyl Compounds by Lithium Amide Bases. Organic Letters 2003, 5 (10) , 1673-1675. https://doi.org/10.1021/ol034348l
  2. Wouter I. Iwema Bakker, Poh Lee Wong, Victor Snieckus, Jeffrey M. Warrington, Louis Barriault. Lithium Diisopropylamide. 2004,,https://doi.org/10.1002/047084289X.rl101
  3. Kazumasa Wakamatsu, Hiroaki Tan, Norikazu Ban, Naotaka Uchiyama, Haruki Niwa, Kiyoyuki Yamada. Isolation of the Strained Bridgehead Enol Ether of a Bicyclo[3.3.1]nonan-2-one System. Chemistry Letters 1987, 16 (1) , 121-122. https://doi.org/10.1246/cl.1987.121
  4. A.J.H. Klunder, W.C.G.M. de Valk, J.M.J. Verlaak, J.W.M. Schellekens, J.H. Noordik, V. Parthasarathi, B. Zwanenburg. Nucleophilic eliminative ring fission of bridgehead substituted 1,3-bishomocubyl acetates. Tetrahedron 1985, 41 (5) , 963-973. https://doi.org/10.1016/S0040-4020(01)96416-6
  5. P.M Ivanov, E Ōsawa, A.J.H Klunder, B Zwanenburg. Computational analysis of the nucleophilic eliminative ring fission of bridgehead substituted 1,3-bishomocubyl acetates. Tetrahedron 1985, 41 (5) , 975-977. https://doi.org/10.1016/S0040-4020(01)96417-8
  6. N.H. Werstiuk. Homoenolate anions and homoenolate anion equivalents. Tetrahedron 1983, 39 (2) , 205-268. https://doi.org/10.1016/S0040-4020(01)91817-4
  7. Kenneth J. Shea. Recent developments in the synthesis, structure and chemistry of bridgehead alkenes. Tetrahedron 1980, 36 (12) , 1683-1715. https://doi.org/10.1016/0040-4020(80)80067-6
  8. D.H. HUNTER, J.B. STOTHERS, E.W. WARNHOFF. Rearrangements in Carbanions. 1980,,, 391-470. https://doi.org/10.1016/B978-0-12-481301-4.50012-7
  9. K. Yamada, Y. Kyotani, S. Manabe, M. Suzuki. Total synthesis of (±)-patchouli alcohol and (±)-seychellene via a common homoisotwistane intermediate. Tetrahedron 1979, 35 (3) , 293-298. https://doi.org/10.1016/0040-4020(79)80064-2
  10. Kiyoyuki Yamada, Shunichi Manabe, Yoshinori Kyotani, Masaaki Suzuki, Yoshimasa Hirata. Conformational Effect on the Bridgehead Reaction of Bicyclo[3.3.1]nonan-2-ones. A Facile Bridgehead Deuteration of a Bicyclo[3.3.1]nonan-2-one Derivative with the Cyclohexanone Ring Locked in the Boat Conformation. Bulletin of the Chemical Society of Japan 1979, 52 (1) , 186-190. https://doi.org/10.1246/bcsj.52.186
  11. Edwin M. Kaiser. Heavier alkali metals annual survey covering the year 1975. Journal of Organometallic Chemistry 1977, 130 , 133-155. https://doi.org/10.1016/S0022-328X(00)92257-5
  12. ALEX NICKON, DOUGLAS F. COVEY, FU-CHIH HUANG, YU-NENG KUO. ChemInform Abstract: AN UNUSUALLY FACILE BRIDGEHEAD ENOLIZATION, LOCKED BOAT FORMS IN ANTI-BREDT OLEFINS. Chemischer Informationsdienst 1975, 6 (18) , no-no. https://doi.org/10.1002/chin.197518202

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