Photochemical reactions. Part III. Thermal generation of photoenols and their derivatives from substituted 1,2-dihydrobenzocyclobutenes
- 1 January 1974
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 409-414
- https://doi.org/10.1039/p19740000409
Abstract
On heating, 1,2-dihydrobenzocyclobuten-1-ol and its derivatives undergo an electrocyclic, conrotatory ring opening to form the corresponding o-quinonedimethide species in which the oxygen substituent always adopts the (E)-configuration. The dimethide species can be trapped with a variety of dienophiles, including maleic anhydride and quinones. These trapping experiments prove that the o-quinonedimethide species produced thermally are identical with the photoenols formed during the irradiation of o-alkylaromatic ketones. The rate of ring opening of substituted benzocyclobutenols depends on the electronic nature of the substituents as well as their size.Keywords
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