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Dibenz[ b,f ]oxepin and thiepin radical anions. Conjugative properties of sulfur in its different oxidation states
Author(s) -
Leardini R.,
Placucci G.
Publication year - 1976
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.5570130215
Subject(s) - chemistry , sulfoxide , sulfur , sulfone , sulfonyl , sulfide , medicinal chemistry , ion , radical , radical ion , photochemistry , dimethyl sulfoxide , organic chemistry , alkyl
Abstract The radical anion of dibenz[ b,f ]oxepin has been investigated by esr spectroscopy and the relative coupling constants compared with dibenzo[ b,f ]thiepin. In both cases assignments were obtained using a theoretical method (INDO). In addition radicals from dibenzo[ b,f ]thiepin sulfoxide and sulfone could be detected and, unusually, the free electron density on carbon atoms of the radical anion containing a sulfonyl group is larger than that on carbons of radical anions containing a sulfide or a sulfoxide group.