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MIGRATION D'UNE DOUBLE LIAISON SOUS L'EFFET D'UN GROUPEMENT CARBOXYLE
Author(s) -
Klein J.
Publication year - 1963
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.196300048
Subject(s) - chemistry , hydrobromic acid , cyclohexene , acetic acid , nitrile , halogenation , acetonitrile , hydrolysis , bromine , medicinal chemistry , bromide , carboxylic acid , organic chemistry , catalysis
Cyclohexene‐1‐acetonitrile (II) yields on prolonged treatment with hydrobromic acid a brominated acid, which gives on dehydro‐bromination cyclohexene‐3‐acetic acid (VI) characterized by its iodolactone. The acid VI was synthesised by an Arndt‐Eustert homologation of cyclohexene‐3‐carboxylic acid (VII), and by reduction of (VII) to the carbinol (IX) which was transformed into the bromide (X). Reaction of (X) with magnesium and then with carbon dioxide gave (VI). The tosylate of (IX) was also converted into the nitrile (XI), which was hydrolyzed to (VI).