Rearrangement of a barrellene oxide to an isocoumarin under flash thermolysis conditions. An apparent series of sigmatropic shifts
- 15 March 1977
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 55 (6) , 975-978
- https://doi.org/10.1139/v77-136
Abstract
Flash thermolysis of dimethyl 3-oxatricyclo[3.2.2.02,4]nona-6,8-diene-6,7-dicarboxylate (the oxide of barrellene-2,3-dicarboxylic acid dimethyl ester) (2) at 700 °C gave methyl isocoumarin-7-carboxylate (3) as a major component of the thermolysate. The rearrangement is discussed in terms of sigmatropic shifts in cycloheptatrienes and their norcaradiene tautomers.Keywords
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