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Studies on the synthesis of heterocyclic compounds. XI. Cleavage of 1,3‐benzodioxoles by magnesium bromide‐acetic anhydride
Author(s) -
Bonsignore Leonardo,
Fadda Anna Maria,
Loy Giuseppe,
Maccioni Antonio,
Podda Gianni
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200339
Subject(s) - chemistry , acetic anhydride , magnesium bromide , reagent , benzene , cleavage (geology) , bromide , acetonitrile , magnesium , electrophile , hydrolysis , organic chemistry , ring (chemistry) , electrophilic substitution , medicinal chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
The cleavage reaction of some 1,3‐benzodioxole derivatives with magnesium bromide and acetic anhydride has been studied. The reactions have been carried out in acetonitrile solution at room temperature. In all of the 1,3‐benzodioxoles studied, the opening of the heterocyclic ring with formation of bromides, alkenes and their corresponding products of hydrolysis have been observed. The competitive electrophilic substitution on the benzene ring was very limited and was insignificant when a large excess of the cleavage reagent was used. The structures of newly prepared compounds have been determined by elemental analysis, spectroscopic data and comparison with authentic samples.