These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.


Pubmed for Handhelds

PUBMED FOR HANDHELDS

Search MEDLINE/PubMed

  • Title: Aromatization of the A-ring of norethynodrel, a steroidal oral contraceptive, during trimethylsilylation.
    Author: Thompson RM, Horning EC.
    Journal: Steroids Lipids Res; 1973; 4(3):135-42. PubMed ID: 4360046.
    Abstract:
    Treatment of the steroidal oral contraceptive, norethynodrel (Ia), under persilylation conditions with trimethylsilylimidazole yielded two products: 17 alpha-ethynyl-3,5(10)-estradien-3, 17 beta-diTMS (IIa) and 17 alpha-ethynyl-1,3,5(10)-estratrien-3,17 beta-diTMS (IIIa). Extended reaction time at 100 degrees C yielded only IIIa, the aromatic substance. A second steroid, 5(10)-estren-17 beta-ol-3-one (LB), gave the corresponding (IIb (iib and IIIb). Both aromatic compounds were characterized by gas chromatography-mass spectrometry comparisons with the diTMS-derivatives of the corresponding estradiols. The mechanism of the aromatization reaction is unknown, but was probably one of dehydrogenation rather than of oxysilylation followed by loss of trimethylsilanol and aromatization.
    [Abstract] [Full Text] [Related] [New Search]