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Proton Acid‐induced Rearrangements of α‐Alkynylestradiol Methyl Ethers
Author(s) -
Pindur Ulf,
Schall Thomas
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301176
Subject(s) - chemistry , deuterium , sulfuric acid , proton , ether , catalysis , acid catalysis , medicinal chemistry , organic chemistry , nuclear physics , physics
When subjected to proton catalysis, the α‐alkynylestradiol methyl ethers 1a and 1b furnish the Rupe or Meyer‐Schuster rearrangement products 2 , 4 , and 5a . In the presence of sulfuric acid, α‐ethynylestradiol 3‐methyl ether ( 1a ) is converted into the D‐homosteroid 3a . The use of deuterated acids gives rise to the formation of the corresponding deuterated steroids 2b , 2c , 3b , and 5b . Some mechanistic implications of these results are also discussed.