Steric Rate‐Retardation in the Chromium Trioxide Oxidation of 4,6‐Dimethyl‐benzocyclobutenol
- 1 January 1970
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 53 (7) , 1869-1873
- https://doi.org/10.1002/hlca.19700530734
Abstract
The rate of oxidation of 4, 6‐dimethyl‐benzocyclobutenol This nomenclature is preferred in the literature [1] [2] to the more systematic name (7‐hydroxy‐3, 5‐dimethyl‐bicyclo [4.2.0] octa‐1,3,5‐triene). (1) with chromium trioxide has been measured. After correction for the influence of the two methyl substituents the rate of oxidation of 1 is lower than that of 1‐tetralol (9) and 1‐indanol (10) by factors of 3 and 5 respectively. The lower oxidation rate of 1 as compared to 9 and 10 is interpreted in terms of a steric rate retardation arising from angle strain in the developing carbonyl function of 4, 6‐dimethylbenzocyclobutenone (4).Keywords
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