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Trityl Propionate and Trityl ~-Naphthoate Ii. Reactions

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Trityl Propionate and Trityl ~-Naphthoate Ii. Reactions I. A STUDY OF PYROLYTIC AND PHOTOLYTIC DECOMPOSITION/OF - TRITYL PROPIONATE AND TRITYL ~-NAPHTHOATE II. REACTIONS OF ORGANOMETALLIC REAGENTS WITH ORTHOESTERS AND ACETALS By BRIJRAJ SINH RATHORE,, Bachelor of Science St, John's College, Agra University Agra, India 1956 Master of Science St. John's College, Agra University Agra, India 1958 Submitted to t.he Faculty of the Graduate School of the Oklahoma State University in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY May, 1964 OKLAHOMA ITATE UNIVERSl1! LIBRARY JAN 8 1005 I. A STUDY OF PYROLYTIC AND PHOTOLYTIC DECOMPOSITION OF TRITYL PROPIONATE AND TRITYL ~-NAPHTHOATE II. REACTIONS OF ORGANOMETALLIC REAGENTS WITH ORTHOESTERS AND ACETALS Thesis Approved: Thesis Adviser ..Y,f -/d - 'fV/ ~ n of the Graduate School 570313 ii ACKNOWLEDGMENTS I· wish to express my gratitude t~ Dr •. K. Darrell Berlin for all .his enthusiasm,.encouragement and patience during my.studies and research • . I also wish to thE(.nk Dr •.• O•. C, .Dermer for his helpful criticism .during the preparatiofi of this thesis • . Thanks ate also acknowledged to.the National Science Foundation for .the grant ofa research assistantship (Februaryl962 toJuly.,1963) , and to the Dow Chemical Company, for a research fellowship (August· 1963 to ~ay · 1964). iii TABLE.OF CONTENTS Page INTRODUCTION . • . • .• • . .. .. • . • • • • • • • • . • . • • •.• 1 Part I. A STUDY OF PYROLYTIC AND PHOTOLYTIC DECOMPOSITION OF TRITYL PROPIONATE AND TRITYL ~-NAPHTHOATE ••••• 2 II. REACTIONS OF ORGANOMETALLIC REAGENTS WITH ORTHOESTERS AND ACETALS • • . • , . • . • , • . • . 80 . iv . INTR,ODUCTIQN Investigations·in two different fields.of organic chemistry are preiented in the two parts of this thesis. Each part has its corres­ ponding chapter on historical, discussion and experimental sections and bibliography, and is complete by itself. The first part:of the thesis concerns the studies on the pyrolytic and photolytic decomposition of trityl esters. Cleavage of such esters was predicted to occur via hemolytic carbon-o~yg;en bond severance at elevated temperatures •. The i,nvestigations provided an opportunity, to study the relative stability of trityl and acyloxy or. aroyloxy, radicals as ~ell as the decay routes of most radicals produced. The second part of the thesis describes investigations on the use of the orthoestets and acetals as the precursors for ~ialkoxy and alko~y­ carbenes •. Dialkoxycarbenes,.although·proposed as intermediates in the formation of orthoesters, have been the most elusive type of carbenes to trap and consequently not studied extensively. Attempts to genet"ate such carbenes and study,-the competitive reaction between compounds having electron-rich centers appeared worthwhile. It was surprising to note that although reactions of orthoesters and acetals withGrignard reagents have been studied, parallel reactions with lithium reagents are unreported. 1 PART I A STUDY OF PYROLYTIC AND PHOTOLYTIC DECOMPOSITION OF TRITYL PROPIONATE AND TRITYL ~~NAPHTHOATE +ABLE OF CONTENTS Chapter Page I. HISTORICAL . , . , . 6 ,Esters of Tertiary Alcohols • • •••. " . 6 Pyrolysis.of Trityl Esters and Related Compounds 11 II. DISCUSSION OF THE RESULTS AND CONCLUSIONS 21 IU. EXPERIMENTAL • • 38 Preparation of Sodium S-Naphthoate 38 Preparation.of Trityl.Bromide •. ~ . ... 38 Preparation of Trityl Propionate (I) 39 Preparation of ~-Naphthoyl Chloride • . ' 40 Preparation of Trityl 1:)-Naphthoate (II) 40 Preparation of Trityl S~Naphthoyl Peroxide 41 Pyrolysis of Trityl Propionate (I) .... 42 Pyrolysis of Trityl Propionate (I) in an Oxygen .Atmosphere • • • • • • • . , . • . • . .. 48 Pyrolysis of Trityl ~-Naphthoate (II) • 49 Second Pyrolysis of Trityl !:)•Naphthoate (II) 53 Pyrolysis of !:)~Naphthoyl Peroxide ••••••. 59 Pyrolysis of !:)•Naphthoyl Peroxide With Triphenyi- methane . , . 61 Pyrolysis of e-Naphthoic Acid ••• , •....•••• 63 Pyrolysi$ of Trityl ~-Naphthoate (II)·in Oxygen 64 Photolysis of Trityl. 1:)-Naphthoate (II) 66 BIBLIOGRAPHY .•.••••.••••.•• ·..•••• 77 3 LIST OF TABLES Table Page I. Qualitative Gas Chromatographic Analysis of the Liquids in the First Trap in the Pyrolysis of I . • . • 43 -II. Quantitative Gas Chromatographic Analysis of the Liquids in the First Trap in the Pyrolysis of I • . , . • 43 III. Qualitative Gas Chromatographic Analysis of the Nonacidic Residue From Pyrolysate of I •• , 45 IV. Pyrolysis of Trityl Propionate (I) (Under Nitrogen) • .. 48 V. Qualitative Gas Chrom~tographic Analysis of the Nonacidic Extract From the Pyrolysate of II • • • • 50 VI. Quantitative Gas Chromatographic Analysis of Fraction .F 55 VII. Pyrolysis of Trityl r,-Na_phtho~te (II) (Under Nitrogen) 57 VIII. Pyrolysis of S~Naphthoyl Pero~ide, •. • e • • e • 0 • 0 0 61 IX. Pyrolysis of S-Naphthoyl Peroxide with Triphenylmethane 63 I x. Pyrolysis of S~Naphthoic Acid •. 64 XI. Pyrolysis of Trityl S·Naphthoate (II) (In Oxygen) . 66 4 LIST OF ILLUSTRATIONS Plate Page Infrared Spectra I. Trityl Propionate (I),. Mull With Nujol 68 II. Copo+ymer of Styrene and Acrylic Acid From Pyrolysis of I, KBr Pellet . • . 69 . III. .Trityl ~-Naphthoate (II)' KBr, Pellet . .. 70 . IV. Polymer A, KBr Pellet . • . .. ... 71 v. Polymer B,. KBr Pellet • • . • . ... 72 VI. Polymer c,. KBr Pellet . •. 73 . Nuclear Magnetic Resonance Spectra VII. Trityl Propionate (I) . .. 74 VIII. Polymer A . - ' . 75 Ultraviolet Spectra . IX. A Comparison of Ultraviolet Spectra ••1111000000 76 -5 .CHAPTER I HISTORICAL Esters of Tertiary Alcohols Syntheses of esters of tertiary alcohols present different and, on a·number of OC<fasions,.difficult problems.· The conventional esterifica- tion reaction with a tertiary alcohol and a carboxylic acid in the presence of an acid catalyst often.leads to dehydration of the alcohol - to give an olefin and/or rearrangell!ent of the carbon skeleton •. Steric considerations alone are a formidable obstacle in the p,rocess. Acetyla- tion of a highly hihdered_-tertiary' hydroxyl ,group · ct:m. be · achieved by · ; , , reaction with ketene which is g_enerated :l;,y, prrt,Hysis of ace torte. -..!""Butyl acetate can .be, prepared from ,!·butyl alcohol' with acetic anhydride, arid zinc chlori,;le (6) or with acetyl chloride in presence of N;N-dimethyl- aniline (30) •. Perhaps a more convenient laboratory method of synthesis of such esters employs the reaction of the corresponding tertiary halide with the silv~r salt of the acid (53)~ .Esters of c~rtain aliphatic ter- tia1;y alcohols'i"~an. be made from the olefln and the corresponding acid as exemplified by the prepa1;ation ·of tertiary butyl acetate from. iso• butylene and glacial acetic acid in pre·sehce of 'zinc chloride (37) or ,6 7 sulfuric acid (40) •. Such an approach is ·not feasible for synthesis of esters of triarylmethanols., .Triphenylniethanol has been known for a.long time, but relatively few of its esters are recorded. Gomberg and Davis (25) were the first to report the synthesis of trityl acetate obtained from trityl chloride and exc~ss silver acetate in boiling benzene. 0 0 II II . benzene .. (C H ) C-0-C-CH . (C 6H5)f-X + M-0-C-CHJ reflux 6 5 3 3 X = Cl, M = Ag This general reaction has been studied and. expanded by a nllll!ber of investigators. Ammonium, sodium and potassium salts (2, 10, 15, 50) have been used in addition.to silver salts with varying.degree of . ~ .. ~-. ~ : ,·· . success •. Trityl bromide, although not readily available,. is more reac- tive and less hygroscopic than trityl chloride (10, 50) . Preparation of trityl formate from triphenylmethanol and anhydrous formic acid by Bowden and Watkins (16) is the only·reported direct synthesis of a trityl ester from the acid and the alcohol. The ester was not is.olated as it was unstable above 49°. Althou~h the mechanism of the esterification was not s4bstantiated,. it was probably ·ionic in nature .. involving the formation and reacti<m of trityl carbonium ion. Trityl acetate has been obtained (95%) by shaking a solution of trityl bromide with ammonium acetate in benzene by Schoepfle (50) •. Trityl propionate · .was also -prepared via the reaction of a.- large excess of silver propion- ate with trityl chloride in boiling benzene (2). Silver benzoate and trityl chloride condensed.in benzene at 60° to give trityl benzoate (15) ·· .. - ,,· . in unspectfied yield .•. 8 0 0 II benzen~ • (CH) C-0-C-RII (C 6~5) 3qc1 + AgO-C-R · 6 5 3 R = C6H5, CH3, c2a5 Andrews and Keefer (2) have prepared trityl acetate and trityl propionate from trityl chloride and the corresponding acid in the presence of S-bromoallyl~,!!~hexylamine as the hydrogen chloride trap. Two mechanisms have been. discussed. In one .case the acid is presumed to. act as an electrophile in establishing the equilibrium in ionization of trityl chloride •. This is followed by reaction of the carbonium ion with the ~arboxylate ariion. It is also possible to consider a concerted mechanism involving attack of the carboxylate anion on carbon and electrophilic solvation of chloride ion. Up to 39 per cent conversion of trityl chlor- ide to the esters was reported. The studies, however, were more from the kinetic rather than synthetic point of view. A change in the general procedure has been reported by Blicke (15) who prepared trityl benzoate from potassium triphenylmethoxide and benzoyl chloride. He noted the reaction was exothermic in benzene solution and obtained trityl benzoate although the yield was not given. Another approach, somewhat specific for preparation of trityl esters, is the reaction of peroxides of carboxylic acids with trityl radicals or triphenylmethane. Wieland and co-workers (56,. 57) have prepared trityl benzoate, trityl .,e-toluate and trityl .,e-anisate by this procedure. Trityl radicals were generated by the reaction of pure trityl chloride 9 with mercury·in benzene solution. Trityl radicals initiate a chain reaction, . as shown. below ... (C 6H5) 3C-Cl .+ Hg 0 0 0 II II II (C H ·) '·c· + 9-c-c H ·---.•~ . (C H ) C-0-C-C. H + C H CO• ,6 5 3 I 6 5 · 6 s 3 6 s 6 s 0-C-C H II 6 s 0 The 1benzoyloxy radical may either react with another trityl radical or it may lose carbon dioxide to give phenyl radical.
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