cis-syn-cis-1,2,4,5-Tetracyclohexylcyclohexane. A moderately crowded saturated hydrocarbon adopting a twist-boat conformation

Journal of Organic Chemistry

Volumn 64, Issue 17, 1999, Pages 6505-6507

  Golan, Oren ^a   Cohen, Shmuel ^a   Biali, Silvio E ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4,5 TETRACYCLOHEXYLCYCLOHEXANE; HEXANE; HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CIS ISOMER; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; ENERGY TRANSFER; HEAT TRANSFER; HYDROGENATION; MOLECULAR INTERACTION; STEREOISOMERISM; STEREOSPECIFICITY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0033588331     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990453q     Document Type: Article

References (15)

1. (a) Conformational Behavior of Six-Membered Rings; Juaristi, E., Ed.; VCH Publishers: New York, 1995.
2. (b) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994.
3. For a review on nonchair conformations of cyclohexane see: Kellie, G. M.; Riddell, F. G. Top. Stereochem. 1974, 8, 225.
4. A cyclohexane 1,4-cis-disubstituted by a quinone and a porphyrin moiety has been shown to adopt a twist-boat conformation, see: Dieks, H.; Senge, M. O.; Kirste, B.; Kurreck, H. J. Org. Chem. 1997, 62, 8660.
5. Weiser, J.; Golan, O.; Fitjer, L.; Biali, S. E. J. Org. Chem. 1996, 61, 8277.
6. Columbus, I.; Hoffman, R. E.; Biali, S. E. J. Am. Chem. Soc. 1996, 118, 6890.
7. For simplicity, the configurational isomers of 3 will be described by the method commonly used for fused-ring cyclohexanes. The mutual disposition of two vicinal groups will be denoted as "cis" or "trans". If the two substituents at the 1 and 5 positions of the central ring are in a mutual cis or trans relationship, this will be denoted by the "syn" and "anti" descriptors, respectively.
8. Allinger, N. L. MM3(92): Technical Utilization Corporation.
9. Weiser, J.; Holthausen, M. C.; Fitjer, L. J. Comput. Chem. 1997, 18, 1264.
10. For a comparison of the rotational barriers of tetraisopropylethene and tetacyclohexylethene see: Columbus, I.; Biali, S. E. J. Org. Chem. 1994, 59, 3402.
11. Harada, K.; Hart, H.; Du, C.-J. F. J. Org. Chem. 1985, 50, 5524.
12. The authors have deposited atomic coordinates for the structures with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
13. For a recent determination of the inversion barrier of cyclohexane see: O'Leary, B. M.; Grotzfeld, R. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 11701.
14. Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783.
15. Derome, A. E. Modern NMR Techniques for Chemistry Research; Pergamon Press: Oxford, 1987; p 221.