Open AccessIpso nitration XXI. Nitration of p-tolylalkanoic acids and derivatives: spiro adducts
Author(s) -
Alfred Fischer,
D. R. A. Leonard,
Rolf Röderer
Publication year - 1979
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v79-405
Subject(s) - nitration , chemistry , adduct , acetic anhydride , acetic acid , organic chemistry , medicinal chemistry , butyric acid , butyrate , lactone , catalysis , fermentation
Nitration of 4-(p-tolyl)butyric acid and of 3-(p-tolyl)propionic acid in acetic anhydride gives good yields of the diasteriomeric spiro lactone adducts 1 and 12, respectively. Nitration of methyl 4-(p-tolyl)butyrate, 4-(p-tolyl)butanol, and 4-(p-tolyl)butyl acetate gives nitronium acetate adducts but does not give spiro adducts.