X-ray Structure Determination of [1-Cyano-2,2-dimethylcyclopropyllithium·Tetrahydrofuran]∞: A Tetrahedral Anionic α-Cyano Carbon Atom

Journal of the American Chemical Society

Volumn 110, Issue 20, 1988, Pages 6925-6926

  Boche, Gernot ^a   Harms, Klaus ^a   Marsch, Michael ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000609569     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00228a073     Document Type: Article

References (22)

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6. Levin, J.-O.; Rappe, C.; Chem. Scr. 1971, 1, 233.
7. A summary on other preparations of α-cyano cyclopropyl anions is given in the following: Boche, G.; Walborsky, H. M. “Cyclopropyl radicals, anion radicals and anions” In Rappoport, Z. The Chemistry of the Cyclopropyl Group; John Wiley & Sons: Chichester, 1987; pp 701-807.
8. A similar conclusion was reached from D/H exchange reactions by van Wijnen et al. (van Wijnen, W. T. H.; Steinberg, H.; de Boer, Th. J. Tetrahedron 1972, 28, 5423-5432).
9. Boche, G.; Marsch, M.; Harms, K. Angew. Chem. 1986, 98, 373-374
10. A similar conclusion was reached from NMR investigations in solution: Bradamante, S.; Pagani, G. A. J. Chem. Soc., Perkin Trans. 2 1986, 1035-1046.
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18. ∞ in the rearrangement of the 9-cyano-cis-bicyclo[6.1.0]nona-2, 4, 6-trien-9-yl anion a vicinal and not the distal C-C bond is broken; Boche, G.; Martens, D. Chem. Ber. 1979, 112, 175-195.
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