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woodwardthesis 博士论文

'woodwardthesis 博士论文'
ASYNTHETICATTACKONTHEOESTRONEPROBLEM by RobertBurnsWoodward B.S.MassachusettsIn8~ituteofTeohnology SubmittedinPartialFulril1men~ot theRequirementsfortheDegree of DOCTOROFPHILOSOPHY fromthe MassaohusettsInstituteofTechnology 1937 SignatureofAuthor-.??????-_ DepartmentorChemistry,Kay13,1931 SignatureorChairmanofDepartme~£ CommitteeonGraduateStudent8/,~_._ ~(-. ACKNOWLEDGID~mNT INTRODUCTION????????????????????,.? ?? ? ?? ? ?? ???1 I.PUBLICATION??????.??????????????????????-.;5 General??????????????????????????????3 Experimental??????????????????????????11 O(-phenyl~~(2-furyl-)-acrylicnitri'le11 2-(~-phe~lethyl-)-fur~~e????????????11 ot-phenyl-(3~(2-furyl-)ethylene?????12 Hydrogenation????????????????13 Dibromide?-.? ? ? ? ? ? ? ? ? ? ?? ? ? ? ??13 m-methoxybenzaldehyde??????????.?????13 m-methoxybenzylalcohol???????.??????14 m-methoxybenzylbromide??????????????14 m~methoxyphenylacetonitrile15 c forsometime,evenafterseveraldistillationsinvacuo. Afterrefluxinginacetonesolutionoverpotassium~an1de “for sometime,however,thesubsl,ancewasrecovered,sub- stantiallyunchanged,withtheexceptionthatitwasnowper- :rectly“stable,andgaveanexcellentyield(88%)ofthecorr- esponding·nitriteontreatmentintheusualmannerwithaequ- ~ous-alcoholicpotas8iumcyanide.Itispossiblet~~a high~.react!veimpurity,capablea'teat.aly~ingether-:rorma~ tionand~droly81sinthepreparationoft~enit.rite,was r~ovedbyth.eacetone-potassiumcyani,detreatme~. Thecon“densa“t:l.oDof18-methoxy-pheDT~acet.on1tr1a:e .''_0-“- with'1'\trfUraltoat-(m-methoxyphenyl-).[3-(2-furyl-)- acrylicn1trii.8(IV: R ?OCHa)proceededsmoothly:thepro- duct,an011,mayi:rdesiredbeisolated-byd1st,illationin vaeuo,butitwas moreconvenientfor8lDthet1cwo~k,reduce 8. thecrudecondensationproduotdire~t~bymoltensodium andabsolutealcoholto2-({3.,(m-methoxy-phenyl-)-ethyl-) fUrane(III:R~·OCHa). 2 -(f3-phenylethy~-)-1Uranereactedonlong standingwithp~remaleicanhydrideinanhydrousetherto giveabeautifullycrystallineadditionproduct,3 -(f3- phenylethyl.).3,6-endoxo-~6.cyclobexene-l,2-dicarbox- yl~canhydride(IX: R=H).~theotherhand,.itthere- action-mixturewasirradiatedwithultra-violet11ght,re actiontookplacemuch morerapidly,with-theformation.of aditreRent,h1gher.eltiqgadditionproduct.Thelat~8r ~-additionproductwasalaoformed·whenanetherealBolu- tion~the.«-addit.ionproductwasirradiated.Botho~the ·1 substancesonheaf,1ugabovethemelt,1ngpoint.aloaeQI'ill solvents~1.8oc1at.dintotheiro.0mp8aent.s.,ODdisaolv!ng in1igroin,particularly,aclear801~t.lon.uobtainedwhieb dEt-P08it.edcrystal.ofmaleicIIJIll7dr14eoD_tandingintheice- bO:x:~:AgaiD,“til.:,olorles.891ut,io~ia-timetJvlan11ine-onheat- ingdeY.lopedthecharact,erlstiaoraugeco.lor.-rmaleicanhy- drideinthta·reag~IntheG“.o~theot--add1“t1onp~et, a:.'bromohydr0X3derlvativewas.»~aredandcharacterized?. ~.~1~11arph8lloaenaareob8~e4“in~h.rctiODo~· 2-(~-(m-methQX7pbelQ'l-)-et~l-).t'Uranewithmale~can­ b7~:1d.TwoadcUtionproduct.,.3-(~(m.t~Q:,pb~l-)- -_._.?'“““'““,~,!!“'·--r--???.““,-.-“_.__~_._---_.__ __.~---“,'??“',“'“,,~--~
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woodwardthesis博士论文
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