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Steroids, XXXVIII. Neighbouring group participation, IX. Preparation of 16α‐hydroxymethyl‐3‐methoxyestra‐1,3,5(10)‐trien‐17α‐ol and solvolysis investigations
Author(s) -
Schneider Gyula,
Hackler László,
Sohár Pál
Publication year - 1988
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.198819880711
Subject(s) - solvolysis , chemistry , hydroxymethyl , acetic acid , medicinal chemistry , group (periodic table) , organic chemistry , stereochemistry , hydrolysis
Solvolysis of the p ‐toluenesulfonate 1d in acetic acid and in dimethyl sulfoxide yields 5b with inversion at C‐17. The conversion can be explained by a neighbouring group participation characterized by the general symbol (AcO‐6). In order to confirm the participation of the 16α‐acetoxymethyl group in 1d , comparative solvolytic investigations were carried out with the toluenesulfonate 9 .