Tetrahedron p. 5431 - 5442 (1987)
Update date:2022-07-29
Topics:
Mann, John
Wilde, Philip D.
Finch, Mark W.
A number of 1-aryl-1-bromopropanones have been prepared and converted into the corresponding oxyallyl carbocations.These were reacted with furan to produce the expected 2-aryl-8-oxabicyclo<3.2.1>oct-6-en-3-ones, as well as a number of interesting side-products.These included 3-aryl-propanoic acid esters produced via Favorskii rearrangements.Attempts to cleave the ether linkage in the cycloadducts using bromotrimethylsilane produced instead 1-aryl-3-furylpropanones in excellent yield.
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