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

Article abstract of DOI:10.1007/BF01221900

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), a β-orientated benzyloxy 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.