Syntheses and structures of 3-stannylcholest-5-ene species

Heather J. Buchanan, Philip J. Cox, Solange M.S.V. Doidge-Harrison, R. Alan Howie, Marcel Jaspars, James L. Wardell*

*Corresponding author for this work

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Abstract

The compounds, 3α- and 3β-triphenylstannylcholest-5-ene, 1 and 2 respectively, have been prepared stereospecifically in reactions of Ph3SnLi with cholesteryl methane- or toluene-p-sulfonates, and of Ph3SnCl with the Grignard reagent from cholesteryl chloride, respectively. Complete 1H and 13C NMR spectral assignments for 1 have been obtained using HMBC and HMQC techniques: these have been used to aid the 13C NMR spectral assignments for 2 and 3α- and 3β-(InPh3-nSn)cholest-5-enes (n = 1-2) (9-12). Crystal structure determinations of 3α-(IPh2Sn)cholest-5-ene 9 and 3α-(I2PhSn)cholest-5-ene 10 indicate distorted tetrahedral geometries about the tin centres in both compounds. The Sn-I bond lengths are 2.731(5) Ȧ in 9 and between 2.6979(12) and 2.7173(12) Ȧ in 10. Despite the similarity in the values (ca. 60°) of the dihedral angles, Sn-C(3)-C(2)-C(1) [C(1) aliphatic carbon] and Sn-C(3)-C(4)-C(5) [C(5) olefinic carbon], the values of 3J[119Sn-13C(1)] are about twice the 3J[119Sn-13C(5)] values in each of 1, 9 and 10; in contrast, 3J[119Sn-13C(1)] and 3J[119Sn-13C(5)] values are essentially the same in each of 2, 11 and 12 [Sn-C(3)-C(2)-C(1) and Sn-C(3)-C(4)-C(5) ca. 180°].

Original languageEnglish
Pages (from-to)3657-3664
Number of pages8
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number24
DOIs
Publication statusPublished - 21 Dec 1997

ASJC Scopus subject areas

  • Chemistry(all)

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    Buchanan, H. J., Cox, P. J., Doidge-Harrison, S. M. S. V., Howie, R. A., Jaspars, M., & Wardell, J. L. (1997). Syntheses and structures of 3-stannylcholest-5-ene species. Journal of the Chemical Society - Perkin Transactions 1, (24), 3657-3664. https://doi.org/10.1039/a703596i