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Part I. the Effect of Ultraviolet Light Upon Some Organic Compounds, Part II. the Synthesis of Amino Compounds Lloyd L

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Part I. the Effect of Ultraviolet Light Upon Some Organic Compounds, Part II. the Synthesis of Amino Compounds Lloyd L Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1930 Part I. The effect of ultraviolet light upon some organic compounds, Part II. The synthesis of amino compounds Lloyd L. Heck Iowa State College Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Organic Chemistry Commons Recommended Citation Heck, Lloyd L., "Part I. The effect of ultraviolet light upon some organic compounds, Part II. The synthesis of amino compounds" (1930). Retrospective Theses and Dissertations. 14760. https://lib.dr.iastate.edu/rtd/14760 This Dissertation is brought to you for free and open access by the Iowa State University Capstones, Theses and Dissertations at Iowa State University Digital Repository. It has been accepted for inclusion in Retrospective Theses and Dissertations by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. INFORWIATION TO USERS This manuscript has been reproduced from the microfilm master. UMI films the text directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer. The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bieedthrough, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. Oversize materials (e.g., maps, drawings, charts) are reproduced by sectioning the original, beginning at the upper left-hand comer and continuing from left to right in equal sections with small overlaps. ProQuest Information and Learning 300 North Zeeb Road, Ann Arbor, Ml 48105-1346 USA 800-521-0500 NOTE TO USERS This reproduction is tlie best copy available. UMI" I THE EXPECT OJ? ULSk&YIOLET LIGHT UPOI SOME OEGmC COilPOUlSS PAHT II THE SYJ3IHESIS OB" liiLEUO COMiOUSDS BY Lloyd L- 3eci: A Thesis oabniitted to the Srsduate faculty for the Pegree cf IX)C!I!OR Of PHELOSOPH? Magor subject—Organic Chemistry Signature was redacted for privacy. In charge of ^jor work. Signature was redacted for privacy. Head of Magor Department. Signature was redacted for privacy. Dean of Graduate College. Iowa State College 1930 UMi Number: DP14458 UMI UMl Microform DP14458 Copyrigiit 2006 by ProQuest Information and Learning Company. All riglits reserved. This microform edition is protected against unauthorized copying under Title 17, United States Code. ProQuest Information and Learning Company 300 North Zeeb Road P.O. 60x1346 Ann Arbor, Ml 48106-1346 ACiaJ0?n:*EDGMI32, The author wishes to express his appreeiation to I)r« Henry Oilman for the suggestion of these 'proMems and for the generous advice and encourage- ^ ment given during the progress of this v^ork. \ 35X0 couaiEiras I THE E2^EC2 05* UL2RiVI0LE2 LIGHS iJM SOME C-EGASIC COMIOUIDS ^ 1 IITE0I>I]C2I025 2 DESCKIPJIOI 05" APPARlOffS 6 EKPERIMES^iL — 8, ALkylmagnesiaia Ealides Under Influence of Ultraviolet Light. See SABLE I 12 See also fABLE III 19 Arylmagnesium Halidea Under Influence of Ultraviolet Light. See TABLE II 17 Attempts to Prepare Phenylmagne si ma Chloride Under Influence of Ultraviolet Light 23 Unsym<» Diphenyl Ethylene, ?7ith Phenyl- magnesium Bromide Under the Influence of Ultraviolet Light 24 The Effect of Ultraviolet Li^t Upon Tetra-£-tolyl Ethylene 26 The Effect of Ultraviolet Light Upon i^rylacrylic Acid — 27 Attempt to Form Qrignard Eeagent from Li phenyl. Magnesium Iodide and Hagnesium Under Influence of Ultraviolet Li^t —28 LISCUSSIOI 29 smmEY S4 iT COH^PEISS fContinued} PABT II - A urn SYHSHESIS OP JOCISO COiiK>uin>S 35 SfUDIES OS 2?HE MGIUTIOH OP SHE -MgX GK)UP 36 IH!ER0rUC2I0H 36 EKPEHIMEH'IAL 39 Reaction "betv/een Diphenylamine, Ethyl- magnesiam Ciiloride, n-Butyl Alcohol and a-Butyl sulfonate 40 Heaetion "between n-3atyl Alcohol, Methyl- magnesium Iodide7 Siphenylamine» and Ethyl ^.-^Jolo-enesulfonate 4£ Heaetion between Phenol, Meti^lmag- nesium Iodide» Siphenylamine and Ethyl 2,-2!oluenesulfonate — 43 Heaetion between Diphenylamine, Ethyl- magnesiaa Chloride, Phenol aad Ethyl p-Tolaenesalfonate —^ 44 Reaction "between n^-Butyl Alcohol* Methyl- magnesium Iodide and Phenol —45 Eeaction "between Mphenylamine , Ethyl- magnesitua Chloride, ^-Jhiocre sol and Ethyl ^-loluene&ulxonate — — 45 Keaction "between 2r!i?hiaeresol, Etl^l- magnesiim ChloriTe, n-Butyl Alcohol and Ethyl 2,-ToltienesTilfonate 48 Eeaction "between n-Batyl Alcohol, Methyl- magnesixun Iodide, ^."S^iocresol and Ethyl o-Ioluene sulfonate'^ 49 Eeaction "between Phenol, Methylmagnesium Iodide, D-Thiocresol and Eth^l iD-2oluene- sulfonate 50 T GOICDSIISS (Continued) Eeaetion "between 2.-Thi coresol, Ethyl- magnesioia Chloride, Phenol and Ethyl £-foluenesulfonate 51 Ihe Eeaetion "between ^.-Ihiocxesol, Methyl- Iodide, n~Butyl Merc^ptan and Ethyl £- Soluenesulfonate 52 The inaction "between n-Butyl Mercaptan» Eti^lmagnesium Chloride, £-Thiocresol and Ethyl ^-Toluenesulfonate —- 52 She Eeaetion "between Diphenylainine, Methyl- mgnesium Iodide, Di-n-Batylamine and Et|yl £-foluenesulf onate — 54 The Eeaetion "between Di-n-Butylamine, Methylmagnesium Iodide .""Diphenylainine and n;-Butyl £-Toluenesulfonate 56 T^ Eeaetion "between lii-n-Butylaaine, Methylaagnesimn Iodide, n-Butyl Mereaptan^ and Ethyl ^-Toluenesol&nat© 58 The Eeaetion Tjetween n-Butyl Mereaptan, i&thylmgnesium Iodide, Bi-n-Butylamine and Ethyl ^-Toluenesulfonate 60 The Eeaetion "between n-Butyl Alcohol, Methyl- laagnesiam Iodide, n-'Sutyl llercaptan and Ethyl ^-ToluenesalTomte —— 60 The Eeaetion "between n-Butyl Mereaptan, JfethylEQagnesium Iodide, n-Butyl Alcohol and Ethyl 2.-Tolaen«sulfonate 61 The Eeaetion between Diphenylamine » Ethyl- magnesiuia Chloride, Siphenylhydroxylaniine and Ethyl ^-Toluenesulfonate 62 The Eeaetion "between £-Thiocresol and Ethyl ^-Toluenesulfonate in Eth^ — — 63 The Eeaetion "between Hi-n-Butylamine and n-B4tyl 2,-2oluenesulfonate in Ether —— 64 yi COUTESTS. (Gontinued) She Reaction "between n-Butyl Mercaptan and n-Butyl ^-Tolaenesulfonate in Ether — 85 DISa'SSlOS 57 A Composite o£ Lsperimental ?^or's:. See IT 68 S'JMMAEY 75 PISH IX - B A STUDY UBO:^ TEZ HEACTIOI 01 -SMgX AID -SI%X COMPOUIDS WITH PHEIIL ISOCY.^^ATE mD PHISYL ISOIHIOCYAHATE 76 ISSHODUCSIOH 76 EIPiaBIESSAL 90 The Eeaation "between Magnesium Bromide Ether ate and Ethyl ;D-Tolaeaesulfonate 90 She Eeaction "between Diphenylamine, Ethyl- magnesium Chloride, Phenyl Isocyanate» Ethyl 2,-2olaenesul±'onate and Magnesium Bromide" Etherate 91 She Heaction Ijetween Diphenylamine, Ethyl- magnesium Chloride» Phenyl Isothiocyanate, Ethyl £-[£oluenesu.lfonate and Magnesiom Bromide Etherate 93 She Eeaction "between ^.-^olylmercaptan. Ethyl- magnesium Iodide, Phenyl Isocyanate, Ethyl _2.-2oluenes.ulfonate and lagnesiusi Bromide Etherate 95 She Eeaction "between jo-Solylmercaptan, Ethyl- magnesixim Iodide and Phenyl Isocyanate 96 She Eeaction "between ^-Solylmercaptan, Ethyl- magnesium Iodide, Phe'nyl Isothioeyanate,> and Ethyl D-Soluenesulfonate 97 rii COIIMTS (Continued) 0?iie Heaction "between _g;-!Dolylniercaptan, Ethylmagnesium Iodide, and Phenyl Isotiiiocyanate 99 BISCSUSSIOI ^ 101 SmSMRY 103 PAB3! I 2HE EFFECT OF ULTHAViaLES LIGH3? UK>3Sr SOME OHSASIC COMPOinSDS IlSaODUCTIOH j There are almost inmimer^le references in the liter- I ^ ature to work done upon the effect of rays emitted "by I i mercury vapor and other so-called ultraviolet light sources I I on organic compounds. Any attempt to classify or organize J this mass of information would be almost futile and far I I I beyond the scope and magnitude of this undertaking. It was found that there are available two excellent books which will I I give a large amount of general information upon this particu- I lar subject. These are by Ellis and »5ells1 and by Morton2 . I The object of this present -ssork was to advance studies already started by Gilman and co-workers upon the stability of the Srignard reagent toward li^t^ and heat^. An added incentive was the fact that more recently ISae. Hamart Lucas and M. Salmon Legagneur 5 reported that isobutyl chloride (1) ELlis and vVells,' "Chemical Action of Ultraviolet Hays," Ohemical Catalog Company, Sew York. 1935. (2) Morton, "Radiation in Chemistry," L. Van ETostrand Company lev? York, 1938. fS) Gilman and Meyers, Ind. ling. Chem., 15, 61 {192S). I Gilman and Meyers, ibid., 14, 243 {192277 I (4) Gilman and Peteraon, Hec. trav. chem., 247 (1929). {5) Mne. Eamart Lucas and M. ?. Salmon Legagneur, Compt. rend. 186, 59 (1928). could "be changed to tertiary "butyl chloride by means of ultraviolet rays. This stuo^ prompted Gilman and Heels:® to determine whether it would be possible to cause a simi­ lar rearrangement of the corresponding orgsnomagnesium 7 halides . 2fhe conclusion reached was that ultraviolet rays affected isobutylmagnesium chloride and tertiary butyl- magnesium chloride to no appreciable extent inasmuch as any rearrangement was concerned. It mi^t be mentioned in this connection that Berthelot and Gaudechon 7a have reported that zinc diethyl decomposes under ultraviolet light to deposit free "sine and evolve a gas. However mercury diethyl decom­ poses to give free mercury simply by standing in the labor­ atory. In addition to vjork which was
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