- o-quinone methides from 4-allenylcyclobutenones: Synthesis and chemistry
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Selected 4-allenylcyclobutenones ring expand to the corresponding o-quinone methides upon thermolysis in refluxing toluene or benzene. These reactive intermediates were not isolated but trapped to give stable products. The reaction has synthetic potential as a route to highly-substituted phenols, benzofurans, and aryl analogs of hexahydrocannabinol. In addition, a unique rearrangement involving a methyl migration from silicon to carbon of selected 4-[3,3-bis(trimethylsilyl)-1,2-propadienyl]cyclobutenones to give 1,2-benzoxasilols is described. Finally, data are presented that show rapid rotation around the alkylidene bond of o-quinone methides at 30°C and that 2-(1-methylethenyl)phenols are in equilibrium with the corresponding o-quinone methides.
- Taing, Meng,Moore, Harold W.
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p. 329 - 340
(2007/10/03)
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