Improved Syntheses and Some Selective Transformations of 2,2,4,4-Tetrachloro-8-oxabicyclo[3.2.1]oct-6-en-3-ones.


The methyl- and alkenyl-substituted furans 1b-h react with pentachloroacetone (2) and sodium 2,2,2-trifluoroethoxide solution to form the title compounds 3b-h in good yield. With the furans 1i-m bearing an oxygen or a sulfur heteroatom in the side chain, moderate yields are obtained. Dechlorination of the [4+3] cycloadducts 3 with the Zn-Cu couple leads to… (More)


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@article{Sendelbach1999ImprovedSA, title={Improved Syntheses and Some Selective Transformations of 2,2,4,4-Tetrachloro-8-oxabicyclo[3.2.1]oct-6-en-3-ones.}, author={Stefan Sendelbach and R{\"u}diger Schwetzler-Raschke and Andreas Radl and R. Kaiser and Gerhard H. Henle and Hilmar Korfant and Stefan Reiner and Baldur F{\"o}hlisch}, journal={The Journal of organic chemistry}, year={1999}, volume={64 10}, pages={3398-3408} }