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Notizen. Addition von Carbonsäuren an (1 S )‐5,5‐Dimethylbicyclo[2.2.1]hept‐2‐en
Author(s) -
Kirmse Wolfgang,
Brandt Sigrid
Publication year - 1984
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19841170723
Subject(s) - chemistry , trifluoroacetic acid , protonation , deamination , acetic acid , medicinal chemistry , 2 norbornyl cation , hydride , ene reaction , stereochemistry , ion , organic chemistry , hydrogen , enzyme
Addition of Carboxylic Acids to (1 S )‐5,5‐Dimethylbicyclo[2.2.1]hept‐2‐ene Protonation of the title compound 5 induced Wagner‐Meerwein rearrangement and 6,2(6,1)‐hydride shifts, depending on the polarity of the acid (trifluoroacetic, acetic, and 2‐ethylhexanoic acid). The optical purity of 5,5‐dimethyl‐2‐norbornyl esters ( 7 ) exceeded that of 7,7‐dimethyl‐2‐norbornyl esters ( 9 ). The results are interpreted in terms of asymmetric ion pairs which are tighter than those involved in deamination reactions.