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Deschamps NM, Kaldis JH, Lock PE, et al. Alkynylcyclohexanol chairs and twist-boats: Co(2)(CO)(6) as a conformational switch. J Org Chem. 2001;66(25):8585-91doi: 10.1021/jo0108820.
Deschamps, N. M., Kaldis, J. H., Lock, P. E., Britten, J. F., & McGlinchey, M. J. (2001). Alkynylcyclohexanol chairs and twist-boats: Co(2)(CO)(6) as a conformational switch. The Journal of organic chemistry, 66(25), 8585-91. https://doi.org/10.1021/jo0108820
Deschamps, N M, et al. "Alkynylcyclohexanol chairs and twist-boats: Co(2)(CO)(6) as a conformational switch." The Journal of organic chemistry vol. 66,25 (2001): 8585-91. doi: https://doi.org/10.1021/jo0108820
Deschamps NM, Kaldis JH, Lock PE, Britten JF, McGlinchey MJ. Alkynylcyclohexanol chairs and twist-boats: Co(2)(CO)(6) as a conformational switch. J Org Chem. 2001 Dec 14;66(25):8585-91. doi: 10.1021/jo0108820. PMID: 11735541.
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J Org Chem. 2001 Dec 14;66(25):8585-91. doi: 10.1021/jo0108820.

Alkynylcyclohexanol chairs and twist-boats: Co(2)(CO)(6) as a conformational switch.

The Journal of organic chemistry

N M Deschamps, J H Kaldis, P E Lock, J F Britten, M J McGlinchey

Affiliations

  1. Department of Chemistry, McMaster University, Hamilton, Ontario, Canada L8S 4M1.

PMID: 11735541 DOI: 10.1021/jo0108820

Abstract

Treatment of 1-[axial]-(trimethylsilylethynyl)cyclohexan-1-ol with dicobalt octacarbonyl results in a conformational ring flip such that the bulky dicobalt-alkyne cluster moiety now occupies the favored equatorial site. However, when a 4-tert-butyl substituent is present, the coordinated alkynyl group retains its original axial or equatorial position. Complexation of trans-[diaxial]-1,4-bis(triphenylsilylethynyl)cyclohexane-1,4-diol brings about a chair-to-chair conformational inversion such that both cluster fragments now occupy equatorial sites. In contrast, cis-1,4-bis(triphenylsilylethynyl)cyclohexane-1,4-diol reacts with Co(2)(CO)(8) to yield the twist-boat conformer in which the two axial hydroxy substituents exhibit intra-molecular hydrogen bonding. Likewise, the corresponding reaction of cis-1,4-bis(trimethylsilylethynyl)cyclohexane-1,4-diol with Co(2)(CO)(8) leads to a twist-boat, but in this case, the molecules are linked through inter-molecular hydrogen bonds. Eight of these cobalt clusters have been characterized by X-ray crystallography, and the potential use of twist-boats in synthesis is discussed.

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