A Stable Hetero-trans-cyclopentene

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 1-2, 1997, Pages 159-160

  Krebs, Adolf ^a   Pforr, Karl Ingo ^a   Raffay, Walter ^a   Thölke, Bernd ^a   König, Wilfried A ^a   Hardt, Ingo ^a   Boese, Roland ^b  

^a UNIVERSITY OF HAMBURG   (Germany)

^b UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

Cycloalkenes; Enantiomeric resolution; Hydrocarbons; Strained molecules

Indexed keywords

EID: 0030871714     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199701591     Document Type: Article

References (14)

1. a) K. Ziegler, H. Wilms, Justus Liebgs Ann. Chem. 1950, 567, 1-43;
2. b) A. C. Cope, R. A. Pike, C. F. Spencer, J. Am. Chem. Soc. 1953, 75, 3212-3215.
3. M. Squillacote, A. Bergman, J. De Felippis, Tetrahedron Lett. 1989, 30, 6805-6808, and references therein.
4. This influence was previously observed in seven-membered cycloalkynes: A. Krebs, J. Wilke, Top. Curr. Chem. 1983, 109, 189-233.
5. An analogous reaction (reverse Brook rearrangement) was observed earlier in other substrates with lower yields, when sodium was used: J. L. Speier, J. Am. Chem. Soc. 1952, 74, 1003-1010.
6. 4 in addition to the dicarboxylic acid, an eight-membered lactone is formed, which after hydrolysis to the w-hydroxycarboxylic acid can also be oxidized to the dicarboxylic acid.
7. 24Si: C 73.38, H 12.32; found C 73.58. H 12.40.
8. -3. The atoms C4 and C5 were refined with an occupation factor of 0.921 (3). the complementary C atoms were given Isotropic displacement factors in positions, found for an inverted conformation with respect to the double bond, which has also trans configuration. The attached hydrogen atoms are thus in approximately the same position. It was not possible to clearly distinguish between disorder or the presence of a twinned crystal. Further details of the crystal structure investigation may be obtained from the Fachinformationszentrum Karlsruhe. D-76344 Eggenstein-Leopoldshufen (Germany), on quoting the depository number CSD-59366.
9. R. Boese. unpublished results.
10. M. J. Frisch, G. W. Trucks, M. Head-Gordon, P. M. W. Gill. M. W. Wong, J. B. Forcsman, B. G. Johnson, H.B. Schlegel, M. A. Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari. J. S. Binkley, C. Gonzales, R. L. Martin, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart, J. A. Pople. GAUSSIAN 92, Revision B, Gaussian Inc., Pittsburgh, PA, 1992.
11. W. A. König, B. Gehrcke, J. High Res. Chromatoger1993, 16, 175- 181.
12. I. Hardt, W. A. König, J. Chromatogr. A 1994, 666, 611-615.
13. D, Boeckh, Ph.D. Thesis. Universität Munchen. 1986. p. 158.
14. R. Boese, M, Nussbaumer in Correlations, Transformations, and Interactions in Organic Crystal Chemistry, Vol. 7. (Eds. D. W. Jones, A. Katrusiak), Oxford University Press, Oxford, England, 1994. pp. 20-37.