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 sp³ to sp². 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.