芳炔苯硫醚化合物的一鍋合成及機理研究.pdf

1、湖南大學碩士學位論文芳炔苯硫醚化合物的一鍋合成及機理研究姓名：許鋒申請學位級別：碩士專業(yè)：有機化學指導教師：安德烈20100520片炔苯硫瞪化合物的合成殷機理jJf究AbstractSulfurcompounds，especiallySulfllydryl(SH)anditsderiVed—SRcompoundspossessesstrongcoordinatiVecapacity，theycantakeshapeinmonolayer

2、ongoldsurfacebymeansofpolarcovalentbond，therefore，SulfurcompoundshaVeexcitingprospectsinmoleculardeVices，cataIysis，electrochemistry，molecularrecognitionandbiosensorfieIds，andsoonThus，thesynthesisofsulfurconlpoundsisbecom

3、ingtheresearchfbcusofrelatedsubljects、^愚havealreadyusedmethylthiomethylphenylsulfone(MP—S)andaromaticaldehydeasrawmaterials，bywayof“onepotroute’’tosynthesizemethylthioaryldiynesBasedonreadinggreatamountresearchliterature

4、s，thisarticleputsforwardanewmethodtosynthesizephenylthioarylethynesby“onepotroute’Inthisanicle，weuseinexpensiVearylacetophenonesasrawmaterials，throughbrominationtoget僅bromoarylacetophenones，thenwegetphenylthiomethylpheny

5、lketonebydealingwiththiophen01Basedontheunderstandingtotheketoneenoltautomerism，wemadethephenylthiomethylphenylketonestonxontheen01triflatebyusingBuLiandClPO(OEt)2successively，thenacquiredphenylthioarylethyneseriesbythew

6、ayofeliminationreactionThemethodhasfollowingadvantages：accessiblematerials，simplemanipulationandgoodyieldThenewmethodnotonlyhaVefeaturesinemciency，highlyselectiVe，low—priced，simpleoperationandgreensyntheticroute，butalsoc

7、anbeusedtothesynthesisofothersubstituentsulndes(suchasmethylthioarylethyne，ethylthioarylethyne，etc)SothenewmethodcanbewidelyusedInordertooptimizethereaction，thisaIrticlenarratesseriescomparatiVetestsinthethirdchapterandc

8、onsultsexistingexperiencesinourlaboratoryestablishtheoptimalconditionsPhenylthiomethylphenylketone(1eq)dissolVedindryTHFunderargonwascooledto一78℃，thenBuLi(12eq)wasaddeddropwiseThereactionmixturewasstirredfor30minat78℃and

9、thenClPO(OEt)2(12eq)wasaddeddropwiseThemixturewasallowedtowarmtoomtemperatureandthenwasstirredfor60min，afterthis，LDA(25eq)wasaddeddropwiseat78℃，Thereactionmixturewasstirredfor60minPurincation0ftheresiduebynashchromatogra