Isomerization of trans-diethylstilbestrol to pseudo-diethylstilbestrol

Article abstract of DOI:10.1016/0039-128X(81)90057-X

This study reports the formation and isolation of a diethylstilbestrol-dimethylsulfoxide (DES-DMSO) adjunct and Z-3,4-di(p-hydroxyphenyl)-2-hexene (ψ-DES) from trans-DES.The presence of ψ-DES was indicated by NMR and mass spectrometry and confirmed by direct comparison to a reference sample.High resolution NMR (360 MHz) along with the comparison of the chemical shift values of methine and methyl protons attached to carbon-carbon double bonds in Z and E isomers of 3-substituted-2-pentenes and dienestrol derivatives were used in postulating the Z-stereochemistry for ψ-DES.A NMR additive increment method was useful for the comparison of the chemical shift values of methine protons in ψ-DES and other literature compounds.Nuclear Overhauser Enhancement (NOE) confirmed the Z-stereochemistry of ψ-DES.