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Bicyclo[3.2.1]octane Synthons from Cyclopropenes: Functionalization of Cycloadducts by Nucleophilic Additions

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https://figshare.com/articles/dataset/Bicyclo_3_2_1_octane_Synthons_from_Cyclopropenes_Functionalization_of_Cycloadducts_by_Nucleophilic_Additions/3352339
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It has been known for several decades that a highly functionalized family of tetrahalobicyclo[3.2.1]octadienes are readily available through the cycloaddition of furan or cyclopentadiene with either tetrachloro- or tetrabromocyclopropene. However, the application of these highly functionalized building blocks in synthesis has remained relatively unexplored in relation to their better-known counterparts derived through oxyallyl cation additions. As a first step toward utilizing these highly versatile intermediates in synthesis, a study of the addition of various nucleophiles to the halogenated nucleus has been conducted. It has been found that these halogenated systems are amenable to a wide range of functionalizations in high yields and with good selectivities.
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2004-01-23
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