Journal of Organic Chemistry p. 5905 - 5909 (1995)
Update date:2022-08-28
Topics:
He, Hu-Ming
Fanwick, Phillip E.
Wood, Karl
Cushman, Mark
A novel 1,3 O -> C migration of a silyl group accompanied by a deacylation reaction was discovered during the conversion of 2-acetyl-3,17-bis(tert-butyldimethylsilyl)-β-estradiol (4) and 3,17-bis(tert-butyldimethylsilyl)-2-propionyl-β-estradiol (5) to 2,17-bis(tert-butyldimethylsilyl)-β-estradiol (6) in the presence of tetra-n-butylammonium fluoride.A crossover experiment indicated that the transformation is intramolecular.
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