Synthesis and reactions of 2-aryl-8-oxabicycloc[3.2.1]oct-6-en-3-ones |
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| Affiliation: | 1. Department of Applied Mathematics I. University of Seville Spain;2. Department of Computer Architecture and Technology University of Seville Spain;1. College of Chemistry, Jilin University, Qianjin Street 2699, Changchun 130012, China;2. School of Chemistry and Life Science, Anshan Normal University, Ping''an Street 43, Anshan 114005, China |
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| Abstract: | 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-oxabioyclo[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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