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Crystal and molecular structure of the product from solvolysis of DHEA tosylate in benzyl alcohol

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Abstract

The crystal and molecular structure of the product from the solvolysis of dehydroepiandrosterone (DHEA) tosylate has been determined by X-ray analysis,1H-NMR, IR, UV, and mass spectrometry. The compound was obtained from DHEA via the 3β-tosyl derivative by refluxing in benzyl alcohol (containing dried potassium acetate) for 12 hr. X-ray analysis shows a planar cyclopropane ring at C(3), C(4), C(5), aβ-orientated benzylozy group attached to C(6) and a benzylidene group attached to C(16). Spectroscopic evidence for the presence of these features in the steroid nucleus are presented and details of the synthesis and possible mechanisms of formation are also discussed.

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References

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Authors and Affiliations

  1. School of Pharmacy, Robert Gordon's Institute of Technology, Schoolhill, AB9 1FR, Aberdeen, Scotland

    Philip J. Cox

  2. School of Applied Sciences, Robert Gordon's Institute of Technology, St. Andrew St., ABI 1HG, Aberdeen, Scotland

    Neil S. Stewart

  3. Chemistry Department, University of Aberdeen, Meston Walk, AB9 2UE, Old Aberdeen, Scotland

    Alan B. Turner & R. Alan Howie

Authors
  1. Philip J. Cox
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  2. Neil S. Stewart
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  3. Alan B. Turner
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  4. R. Alan Howie
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Cox, P.J., Stewart, N.S., Turner, A.B. et al. Crystal and molecular structure of the product from solvolysis of DHEA tosylate in benzyl alcohol. Journal of Crystallographic and Spectroscopic Research 20, 577–581 (1990). https://doi.org/10.1007/BF01221900

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  • DOI: https://doi.org/10.1007/BF01221900

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