SYNTHESIS AND REACTIONS OF 2-ARYL-8-OXABICYCLOOCT-6-EN-3-ONES

Article abstract of DOI:10.1016/S0040-4020(01)87724-3

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.