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Cu?OAc?2·H2O Or Cs2CO3-Promoted ?-alkynyl Elimination Of Propargylic Alcohols

Posted on:2014-09-09Degree:MasterType:Thesis
Country:ChinaCandidate:Z Y HuangFull Text:PDF
GTID:2371330491454163Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
?-carbon selective elimination reaction occurs in various cyclic and acyclic systems,which can be achieved many conversions by ring-opening or ring-expansion,cleavage or addition.Many organometallic intermediates formed during some reactions can be used as the reactive precursors of subsequent reaction to construct many meaningful tandem reactions.Thus,the reaction can be utilized as one of fundamental and effective tools in organic synthesis and organometallic Chemistry.The first chapter,we describe the progress of ?-carbon elimination reaction,especially,introduce and analyze palladium,rhodium,nickel and other metal salts to promote ring-opening,ring expansion and addition reaction via P-carbon elimination in recent years.In the second chapter,we synthesized a series of ?-hydroxy-propargyl alcohols,and a,a-diaryl propargyl alcohols by an addition reaction of Alkynyl lithium with corresponding aryl carbonyl compound.The third chapter,we studied ? or ?-hydroxy propargylic alcohols undergo tandem C(sp)-C(sp3)bond cleavage via ?-alkynyl elimination and homocoupling of the resulted alkynyl species in the presence of Cu(OAc)2-H2O to produce the corresponding hydroxycarbonyl compounds and 1,3-butadiynes.we also studied catalytic amount of Cs2CO3 to promote a,a-diaryl propargyl alcohols' C(sp)-C(sp3)bond cleavage via ?-alkynyl elimination.These studies provide new ways for ?-alkynyl elimination of propargyl alcohols,and also provide new ideas for constructing many tandem reactions which based on ?-alkynyl elimination.
Keywords/Search Tags:C(sp)-C(sp~3)bond cleavage, ?-alkynyl elimination, homocoupling, 1,3-butadiynes, propargylic alcohols
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