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Pentatomie heteroaromatic cations. Note II . Chemical properties of 2‐phenyl‐1,3‐benzoxathiolium perchlorate
Author(s) -
Degani Iacopo,
Fochi Rita,
Tundo Piero
Publication year - 1974
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.5570110411
Subject(s) - chemistry , perchlorate , reagent , lithium aluminium hydride , nucleophile , medicinal chemistry , hydroxide , phenylmagnesium bromide , electrophile , organic chemistry , morpholine , thiophenol , inorganic chemistry , ion , catalysis
The reactions of 2‐phenyl‐1,3‐benzoxathiolium perchlorate with common nucleophilic reagents (water, sodium hydroxide, ethanol, thiophenol, morpholine, phenylmagnesium bromide), with reducing agents (zinc, lithium aluminium hydride) and with manganese dioxide, were studied. In every case the reactions proceed by attack of the reagents at the C‐2 position of the cationic system, giving rise either to 1,3‐benzoxathiole derivatives or to ring‐opening products. The 1,3‐benzoxathiolium salts were shown to be suitable intermediates for converting the carboxylic acids into aldehydes and ketones.