Event submissions
Published
This submission belongs to the session a. General Organic Synthesis of the event The 18th International Electronic Conference on Synthetic Organic Chemistry
Published date
03 Nov, 2014
Citation
Mariam Al Azani, John P Graham, Thies Thiemann, Preparation and Photochemistry of 3-O-Methylestra-1,3,5(10)-Triene-17beta-yl Cinnamates and 3-O-Methylestra-1,3,5(10)-Trien-17-one O-Cinnamoyl-17-Oximes, in Proceedings of The 18th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2014, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-18-a039
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Preparation and Photochemistry of 3-O-Methylestra-1,3,5(10)-Triene-17beta-yl Cinnamates and 3-O-Methylestra-1,3,5(10)-Trien-17-one O-Cinnamoyl-17-Oximes
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Mariam Al Azani 1
John P Graham 1
Thies Thiemann 2
1. Department of Chemistry, UAE University
2. Department of Chemistry, United Arab Emirates University
Abstract
3-O-Methylestra-1,3,5(10)-triene-17beta-yl (E)-cinnamates and 3-O-methylestra-1,3,5(10)-trien-17-one O-(E)-cinnamoyl-17-oximes were prepared from the reaction of cinnamic acids with 3-O-methylestra-1,3,5(10)-trien-17-beta-ol and 3-O-methylestra-1,3,5(10)-trien-17-one 17-oxime, respectively, in the presence of PPh3-CBrCl3 in an Appel-type reaction. Under photolysis, the steroidal cinnamates underwent E-/Z-isomerisation, while the steroidal O-cinnamoyloximes underwent E-/Z-isomerisation concomitant with cleavage reactions.
Keywords
Steroids
estradiol
cinnamates
O-cinnamoyl oximes
Appel reaction
photochemistry
E-/Z-isomerisation
Manuscript
Mariam-main-file.pdf
Poster
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