A cyclophane bridged by an inwardly pyramidalized olefin

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8125-8128

  Pascal, Robert A ^a   Carter, Meredith L ^a   Johnson, Mark R ^a   Ho, Douglas M ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0030569325     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01889-8     Document Type: Article

References (30)

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10. 2OH).
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12. 3 308.0727.
13. o)]. The structure was solved by direct methods and refined with the SHELXTL PLUS software. The molecule sits on Wyckoff position 4c, thus it is disordered across a crystallographic mirror. Refinement of 115 parameters converged at R(F) = 0.071, wR(F) = 0.078, with goodness-of-fit = 1.59.
14. o)]. The structure was solved by direct methods and refined with the SHELXTL PLUS software. Refinement of 524 parameters converged at R(F) = 0.051, wR(F) = 0.049, with goodness-of-fit = 1.06.
15. 15. Only one of the three similar but crystallographically independent molecules of 1 is illustrated, but the distances and angles quoted are the averages for the three molecules.
16. 16. X-ray crystallography tends to underestimate the length of C-H bonds (Churchill, M. R. Inorg. Chem. 1973, 12, 1213-1214). If the in-methine is assumed to have a 1.07 Å C-H bond length, then the hydrogen atom is 2.22 Å from the aromatic ring plane.
17. 17. The MMX forcefield implemented in PCMODEL V 5.0 was employed.
18. 18. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
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23. 23. Many pyramidalized bridgehead olefins, such as the sesquinorbornenes, for which there is no clear distinction between "inward" and "outward", or transition metal complexes of olefins, in which the metalcarbon bond induces pyramidalization, are not considered here.
24. 24. Krohn, K; Rieger, H.; Hopf, H.; Barrett, D.; Jones, P. G.; Doring, D. Chem. Ber. 1990, 123, 1729-1732.
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27. 2,5]dodeca-1,5-diene is the most extreme example (0.249 Å) (Wiberg, K. B.; Adams, R. D.; Okarma, P. J.; Matturro, M. G.; Segmuller, B. J. Am. Chem. Soc. 1984, 106, 2200-2206).
28. 2,5]dodeca-1,5-diene is the most extreme example (0.249 Å) (Wiberg, K. B.; Adams, R. D.; Okarma, P. J.; Matturro, M. G.; Segmuller, B. J. Am. Chem. Soc. 1984, 106, 2200-2206).
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