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Eliminierungsreaktionen an Kationen in Gasphase II Essigsäureeliminierung aus Androstanylacetaten
Author(s) -
Robbiani Richard,
Seibl Josef
Publication year - 1974
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19740570320
Subject(s) - chemistry , acetic acid , metastability , alcohol , ion , labelling , stereochemistry , ethanol , elimination reaction , medicinal chemistry , computational chemistry , organic chemistry , biochemistry
Elimination of acetic acid from the molecular ions of the epimeric androstanylacetates is investigated applying specific 2 H‐labelling and analysis of metastable transitions. Only 17β‐androstanylacetate eliminates acetic acid in a 1,2‐fashion to an extent of 16%. This contribution is shown to be a specific cis ‐elimination and after comparison with water‐elimination in the corresponding alcohol a McLafferty type mechanism is attributed, which then appears to require a planar transition state.