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Rates of Chromium(VI)‐Oxidation of Benzocyclenols
Author(s) -
Müller Paul
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540729
Subject(s) - chemistry , solvolysis , chromium , acetic acid , reactivity (psychology) , semicarbazone , medicinal chemistry , reaction rate , organic chemistry , inorganic chemistry , catalysis , hydrolysis , medicine , alternative medicine , pathology
The oxidation rate of benzocyclobutenol ( 6 ) and of the homologous alcohols up to 1‐benzocyclo‐octenol ( 7 ) with chromium (VI) has been determined in 90% acetic acid. The rate profile for the oxidation reaction is similar to that obtained for the solvolysis of the corresponding chlorides, and clearly shows a low reactivity for the benzocyclobutenyl skeleton, for reactions in which the hybridization changes from sp 3 to sp 2 . On the other hand, semicarbazone formation occurs faster with benzocyclobutenone ( 6a ) than with the homologous ketones. The implication of these results for the oxidation mechanism is discussed.