High-Pressure Cycloaddition Reaction of Tropone with Furans
- 1 October 1987
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 60 (10) , 3633-3638
- https://doi.org/10.1246/bcsj.60.3633
Abstract
Thermal reactions of tropone with furan and 2-methoxyfuran mainly gave the endo-[4+2] cycloadducts, the kinetically controlled products, at 3000 bar. In the latter case, the product further reacted with tropone to yield 2:1-adducts. On the other hand, the reaction with 3,4-dimethoxyfuran under similar conditions yielded mainly the exo-[4+2] adducts, the thermodynamically controlled products. The predominant formation of the endo-Diels–Alder adducts with furans under the high-pressure conditions may be valuable from a synthetic point of view.Keywords
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