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High Organic Iodine Compounds In Various Cyclic Compound Synthesis Methods Of Research

Posted on:2013-12-21Degree:DoctorType:Dissertation
Country:ChinaCandidate:Y YeFull Text:PDF
GTID:1221330395951518Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
As a green process functionalization of C-H improves the atom economy and reduces the amount of waste generated in organic synthesis. Though the functionalization of C-H bond has been studied for several decades, practical synthetic applications of C-H functionalization in synthesis are still somewhat rare; this technology has long captivated organic chemists. This thesis focused on the functionalization of sp3C-H and sp2C-H by hypervalent organoiodine derivatives. The synthesis of several cycles has been reported.First, under the condition of hypervalent organoiodine derivatives and tetrabutylammonium halo, we investigate the oxidative-cyclization reaction with the substrate of Michael adducts of nitroolefins, chalcones,N-tosylimines with activated methylene compounds and synthesize the aziridines, cyclopropanes, oxetanes, azetidines which are the important structural components of many medicinally and biologically active natural and unnatural substances. We also supposed the plausible mechanism of the reaction. The potential of this reaction system has been evaluated for its mild reaction conditions, high diastereoselectivity, enantioselectivity and adaptability to a wide variety of substrates.Next, we investigate the dearomatization-Michael addition-aromatization strategy of phenols, and develop a new approach to achieve the4-position sp2C-H functionalization of benzofurans. Applying the approach, Furoquinolinones and Angelicin also can be prepared...
Keywords/Search Tags:hypervalent iodine, cycles, oxidative reaction, cyclization reaction, dearomatization
PDF Full Text Request
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