芳香烃氯甲基化反应的综述

X(411105),,Blanc06211263Blanc,CH2ClCH2OHCHOCH2CNCH2NH2CH3CH2R,[1,2][3],,,1111HCHO(HCHO)3(HCHO)nHCl,,,LyushinHCHO2HCl6221142,HCHO13,80%7[4]2162HCHO2HCl,460%,Na2SClCH2CO2R,[5]42HCHO2HCl,2[6]HCHO2HCl,270%[7,8]Ootsuka(HCHO)32HCl,H3PO4,904h,2,621,571%,,[9](HCHO)n2HCl,6217%22[10]65017%,[11]C1C12,,PöO[12]218226,,[13]É(R1=R3=ClCH2,R2=H)Ê(R1=R3=ClCH2,R3=H)1999113ChemicalResearchandApplicationVol.11No.31999X199864,19981123112ClCH2OCH3(ClCH2)2OHCHO2HCl,,,[14],PopovClCH2OCH3,Cl2CH2,606h,2,717%[15]PinnellClCH2COH3[16],60%H2SO4,ClCH2OCH35560,24h,Thioflavone[17](ClCH2)2O,3,3[18]Tashiro(ClCH2)2O[19,20,21]É(R=H,R=CH2Cl)Ê(R=R=CH2Cl)113ClCH2O(CH2)nCH3(ClCH2O)2(CH2)n(n=17),[22],,,GreigClCH2OEt,2[23]NaikF3CCOOH,ClCH2OC4H8Cl,(PEES2PES)[24]Marion2C8H17OCH2Cl,,[25,26]É(n=4,R=H)Ê(n=6,R=CH3)Ë(n=8,R=CH3)114(HCHO)n2HClClCH2O(CH2)nCH3(n=17),ClCH2SiMe3ClSiMe22HCHOCH3OCH2COClCH3OCO2CH2ClClCH2OCH2OCH2ClClCH2SiMe3,,,,Me3SiCH2LiClSiMe32HCHO,ClCH2SiMe3Glaenzer,[27]AlexanderCH3OCH2COClAlCl3,,42399%,,[28],CH3OCO2CH2ClClCH2OCH3,03211,[29]XMeOCO2CH2ClLewisacidXCH2ClX=Cl,Br2211H2SO4HClH3PO4HClH2SO4ClSO3H,,,MoshchinskayaHCHO6090,[30]Allan(HCHO)n2HClbicuculine[31],11322522[32]H2SO4,HCHO2HCl,2,4[33]LedovskikhHClHCHO6228221,32,NaOMeH2öZn2HClKSCN,ClCH2MeOCH2CH3NCSCH2CHO[35]Petrove10,ClSO3H,,,,,,[35,36,37]212ZnCl2SnCl4FeCl3AlCl3CuCl2Lewis,,,GrebenyukZnCl2,ClCH2OCH3,2,[38]Barker,AlCl3,122224,[39]AlCl3ClCH2OCH3,[40]Davydov,,,C6H5CH2Clö(C6H5)2CH2GeCl3DyCl3ErCl3,C6H5RRHMe[41]ErgozhinSnCl4,ClCH2OCH3[42]ThomasSnCl4,ClCH2OCH3,41%,,[43]213,,WeberH2SO4FeCl3,,H2SO4,[44]LyushinHClZnCl2,3,427818%[45],87%[46]Gasanova1323:ZnCl2HCl,,,74%71%,35%,2,43,52801419.6[47]IrabienHCHO2HCl,AlCl3ZnCl2FeCl3SnCl4,F2CH3PO4,FeCl3[48]22242SumitomoChemical,H2SO4HCl,9613%[49]H2SO4CaCl2,7915%[50]214,AkihikoLewis,,,,1[51]1Tab.1EffectofcatalystsonchloromethylationoffluorenesCatalystSolventTime(h)Temp()ProductYield(%)H3PO4ZnCl2TiCl4TiCl4SnCl4ACOHCS2CS2CS2CS218215519,550502550r.t2,72,71,81,81.71747525755,,ZnCl2[52]FeCl3[44]Fe2O3[53],CuCl2,,PhCH=CHCH2Cl[54,55]3,,CH2Cl2CHCl3CCl4C2H4Cl2,ón2C6H14CS2CH3NO2AcOHAc2OC2H5OH,4,465%[56],4,461%[57],4,455%[58],2,18mmolög[59],258000248000[60],2[61],63%[62],35%[63]TakeyaAcOH,HClH3PO4,22,1,42[64]AcOHAc2O,1018[65]4,,,,,Kachurin(HCHO)n2HCl23211,(dimethylstearyltaurobetaine)[66,67]Selv,,,98%,PöO812[68],9616%,100%,[69]5,,,,,;,,[1],(),1995,17(4),82[2]DehaanFD,DjaputraM,GrinstaffMW,KaufmanCR,J.Org,Chem.1997,62(9),2694[3]HamadaB,KaddourO,SafarM.J.Soc.AlgerChim.,1994,4(2),147[4]LyushinMM,HamadaB.DepositedDoc.,1984,928[5]AkhmedzadeDA,ShamkhalovaAA,Sakhnovskaya,EB,BabaevaSG.Azerb.Krim.Zh.,1980,(2),49[6]NudelmanA,PatchornikA.US4244885,1981[7]KormachevVV,MitrasovYN.Fosfororg.Soedin.Polim.,1978,4,23[8]KormachevVV,MitrasovYN.SU630257,1978[9]OotsukaH,TakedyaH.JP05117202,1993[10]MirvissSB.US4501903,1985[11]LurikBB,VolkovYP.Zh.Org.Khim.,1986,22(2),844[12]TakezawaT,KusanoT.NipponKagakuKaishi.,1989,(6),1047[13]TashmukhamedovaAK,StempnevskayaIA.Khim.Geterotsikl.Soedir.,1989,(4),470[14]AmatoJS,KaradyS,SletzingerM,WeinstockLM.Synth.Commun.,1979,9(7),917[15]PoPovG,HaeupkeK.DD295564,1986[16]PinnellRP,KhuneGD,KhatriNA,ManattSL.Tetrahedronlett.,1984,25(33),3511[17],,,,,6023379,1985[18]HannounM,BlazevicN,KolbakD,KaifezF.ActaPharm.Jugosl.,1981,31(2),59[19]TashiroM,NagoH.Chem.Express.,1991,6(3),181[20]TashiroM,NagoH.ChemExpress.,1990,5(9),665[21]TashiroM,NagoH.J.Chem.Res.Synop.,1990,(9),296[22]WarshawskyA,desheA.US4568700,1986[23]GreigJA,SherringtonDC.Eur.Polym.J.,1979,15(9),867[24]NaikHA,MCGrailP.T,MaxkenziePD,PexrsonsLW.Polymer,1992,33(1),166[25]AlmiM,ArduiniA,CasnatiA,PochiniA,UngaroR.Tetrahedron,1989,45(7),277[26]HuangZT,WangGQ,YangLM.Synth.Commun.,1995,25(8),1109[27]GlaenzerB1,CsukR.Carbohydr.Res.,1991,220,79[28]MckillopA,MadidabadiFA,LongDA.Tetrahedromlett.,1983,24(18),1933[29]MasperoF,RivettiF,RomanoVB.BE1005988,1991[30]MoshchinskayaNK,RezmchenkoVV,MarkovNM,OliferVS,ShposhnikovS2,SpodarikBZ,GolovnenkoFP,RevenkoLM.SU727610,1980[31]AllanRD,ApostopoulosC.Aust.J.Chem.,1990,43(7),1259[32]YuZhongheng,CN1088574,1994[33]BogorodskayaLP,PoluboyarinovaAY.Maslo2Zhir.Prom2St.,1983,25[34]LedovskikhVM,ShapovalovaYP.UKr.Khim.3323:Zh.,1990,56(4),406[35]PetrovaRA,BerezinBD.Izv.Vyssh.UchebnZaved.,Khim.Khim.Tekhnol.,1986,29(9),55[36]PettovaRA,PotapovaT1.Izv.Vyssh.Uchebn.Zaved.Khim.Khim.Tekhnol.,1984,27(11),1304[37]PetrovaRA,KhelevinaOG.Izv.Vyssh.Uchebn.Zaved.Khim.Khim.Tekhnol.1993,36(2),102[38]GrebenyukVD,BerkelievaLK,ChebotarevaKD.Izv.Akad.Nauk.Turkm.,Ser.Fiz2Mat.,Tekh.,Khim.Geol.Nauk,1992,(1),105[39]BarkerPL,BahiaC.,Tetrahedron,1990,46(8),2691[40]NissanChemical.IndustriesLtd.,JP58.83651,1983[41]DavydovDV,VinogradovSA.Izv.Akad,Nauk.SSR,Ser.Khim.,1990,(3),706[42]ErgozhinEE,AtshabarovaRB.Izv.Akad.Nauk.Kaz.SSR.Ser.Khim.,1985,(5),84[43]ThomasPJ,PewsRG.US5099(083),1991[44]WeberH,BierK.DD236740,1986[45]LyushinMM,MuganlinskiiFF.Azerb.Khim.Zh.,1985,(5),35[46]DarenS.EP345478,1989[47]GasanovaMM,BabakhanbvRA.Azerb.Khim.Zh.,1979,(2),93[48]IrabienGA,OrtizV.ActasSimp.Iberoam.Catal.,1984,2,1539[49],,6032750,198