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Reductive Cleavage of N-Substituted Benzenesulfonamides and P-Sulfamylbenzoic Acid

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Reductive Cleavage of N-Substituted Benzenesulfonamides and P-Sulfamylbenzoic Acid University of the Pacific Scholarly Commons University of the Pacific Theses and Dissertations Graduate School 1975 Reductive cleavage of N-substituted benzenesulfonamides and p- sulfamylbenzoic acid Robert E. Davenport University of the Pacific Follow this and additional works at: https://scholarlycommons.pacific.edu/uop_etds Part of the Chemistry Commons Recommended Citation Davenport, Robert E.. (1975). Reductive cleavage of N-substituted benzenesulfonamides and p- sulfamylbenzoic acid. University of the Pacific, Thesis. https://scholarlycommons.pacific.edu/uop_etds/ 1869 This Thesis is brought to you for free and open access by the Graduate School at Scholarly Commons. It has been accepted for inclusion in University of the Pacific Theses and Dissertations by an authorized administrator of Scholarly Commons. For more information, please contact [email protected]. ~==-------------- REDUCTIVE CLEAVAGE OF N-SUBS'J,ITOTED -BENZENF-BULFONAMIDES AND p·-SULFAMYLBENZOIC ACID A Thesis Presented to the Faculty of the Graduate School University of the Pacific In Partial Pulfillrnent of the Requ:i.rement for the Degree Master of Science by Robert E. Davenport July 1975 This thesis, written and submitted by ~E. is approved for recommendation to the Committee on Graduate Studies, University of the Pacific. Department Chairman or Dean: Thesis Committee: P~- a~·. Chairman Dated__ --'J~_L---::~~---..;./--'2?--,.'""""""/_....9_7=------~-- 7 I ACKNOWLEDGEMENT ~~ rrhe author wishes to express· his sincere gratitude to Dr G'harles A. Matuszak .for his unceasing encouragement and help during the course of this research. My grateful thanks to Dr. Michael J. Minch and Dr. Herschel G. Frye for their helpful suggestions. I would like to thank Dr. Donald K. Wedegaertner, Chairman of the Chemistry Depe..rtment, and Dr. Enerson G. Cobb, former Chairman of the Chemistry Department, for their help and facilities. Finally, my sincere appreciation to Mrs. Dawn Mallard for an excellent job of typing. TABLE OF CONTENTS PAGE INTR.ODUCriON • 0 • • • • • • • • . •• 0 •••••• 1 RESULTS • ·• . 12 . NJVffi lNTERPRNI'ATION . •· 24 DISCUSSION • • • • • • • • • • & • Q • • ••• 28 SUMMARY AND CONCLUSIONS ••• 0 ••.• . 38 EXPERJJ'.ffiNTAI., • • • • • . • . 40 A. Summary of General Experimental Procedures 40 B. Preparation· of Diphenyl Disulfide • 43 C. Reduction of Benzenesu1fonamide • 43 First Reduction • • · 43 Second Reduction . 45 Third Reduction · 45 Fourth Reduction . 45 F~fth Reduction 46 Sixth Reduction . 1!6 Seventh Reduction 46 D. Preparation of N-Phenylbenzenesulfonamide • ~·7 E. Reduction of N-Pnenylbenzenesulfonamide • • 117 ·First Reduction . • • • • • • • · •. ·• • • · • ~ • • • • 47 Second Reduction • • • . • • • • • • • • • • • • • 49 Third Reduction • • · • 49 Fourth Reduction • • • • • • • • • • • • • • 49 Fifth: Reduction • • • • • • • • • • • • 50 . Si.xth. Reduction • • • • • • • • . 50 Seventh Reduction . 50 F •. Preparation of N,N-Diphenylbenzenesulfonamide 51 G. Reduction of N,N-Diphehylbenzenesulfonamide • 51 First Reduction • •. • •. • .• 51 Second Reduction • • • • • • 53 Third Reduction • • • • • 54 Fourth Reduction • • • • • • 54 . H. Preparation of N-Methyl-N-phenylbenzenesulfonamide . 55 I. Reduction of N-Methyl-N-phehylb~nze~esulfonamide • . 55 First Reduction • . .. 55 Second Reduction . .. ... .•. ' . .. 57 Third Reduction • . .... 57 J. Preparation of N,N-Dimethylbenzenesulfonamide 59 K. Reduction of N,N-J)imet.hylbenzenes~lfonarnj_de 59 Fir•st Reduction • • • • •. • •. · •. •. • •. • • • 59 Second Reduction • • • • • • • • 60 M. Reduction of N-Methylbenzenesulfonamide 61 First Reduction • . 61 Second Reduction .. .. .. 62 Third Reduction • . .. 63 N. Preparation of N,N-Diisobutylbenzehesulfonarnid.e 64 ---~ o. Reduction of N,N-Diisobutylbenzenesulfonarnide 64 First Reduction . 64 Second Reduction 66 Third Reduction • . • . • 66 Fourth Reduction 66 Fifth Reduction • . 66 P. Preparation of N-Isobutylbenzenesulfonamide 68 Q. Reduction of N-Isobutylbenzenesulfonamide 68 First Reduction . ~ . 68 Second Reduction 69 Third Reduction . • • • . • . • • • • • • 69 Fourth Reduction 70 Fifth Reduction . 70 R. Preparation of Lithium SaJt.. of N-Phenylbenzenesulfortamide • . • • • . • • • • • 71 S. Reduction of Lithium Salt of N-Phenylbenz.enesulfonamide 71 First Reduction • . ... 71 Second,Reduction . 72 T. Reduction of p-Sulfareylbenzoic Acid 74 ,First Reduction ... .. 74 Second Reduction 75 Third Reduction .. 75 .FourthReduction. 76 BIBLIOGRAPHY • .. 78 APPENDJ.:X • 81 LIST OF TABlES PAGE 1. Birch Reduction of Benzenesu1fonamide • .13 2. Birch Reduction of N-Pheny1benzenesulfonannde 15 3. Birch Reduction of N,N-Diphenylbenzenesu1fonamide • 16 4. Birch Reduction of N-Methy1-N-pheny1benzenesu1fonamide 17 5. Birch Reduction of N,N-Dimethy1benzenesu1fonamide . 18 6. Birch Reduction of N-Methy1benzenesu1fonamide 18 7. Birch Reduction of N,N-Diisobuty1benzenesu1fonamide 19 8. Birch Reduction of N-Isobutylbenzenesulfonamide. 20 9. Birch Reduction of Lithiwn Salt of N-Phenylbenzenesulfon- arnide 21 10. Birch Reduction of p~Sulfamylbenzoic Acid 22 LIST OF SPECTRA PAGE IRl. Thj.ophenol • 83 IR 2. Diphenyl Disulfide 84 IR 3. Thiophenol from Reduction #1 of Benzenesulfonamide. 85 IR 4. Diphenyl Disulfide from Reaction #1 of Benzenesulfonamide 86 IR 5. Diphenylamine .. ' 87 IR 6. Diphenylamine Recovered from Reaction #1 of N,N-Diphenylbenzenesulfonarnide 88 IR 7. · Partially Reduced Diphenylamine from Reaction #1 of N,N-Diphenylbenzenesulfonamide • 89 IR 8. Partially Reduced Diphenylamine from Reaction #l~ of N,N-Diphenylbenzenesulfonamide . 90 NMR 1. Thiophenol . e ~, o 91 NMR 2. Diphenyl Disulfide • 92 NMR 3. Thiophenol (with Diphenyl Disulfide) from Reaction .#1 of Benzenesulfonamide • 93 NMR 4. Partially Reduced Diphenylamine fr~o~m:__R~e~a~c~t'_:l:i~on~------;:T."------ (_________ -Ttu· 4-ef-N-,N=B::i::pherry1b-enzenesul1·onamide . 94 NMR 5. 1,4 Dihydrobenzoic Acid (Student Prepared) • 95 NMR 6. p-Sulfamylbenzoic Acid 96 NMR 7. Product From Reaction #1 of p-Sulfamylbenzoic Acid 97 i' NMR. 8. Product from Reaction #2 of p-Sulfamylbenzoic Acid 98 NMR 9. Product from Reaction #3 of p-Sulfamylbenzoic Acid 99 NMR 10. Product from Reaction #4 of p-Sulf~~lbenzoic Acid . 100 NMR 11. Diphenylamine • 101 --------- -··------" INTRODUGriON .ArnriDnia solutions of alkali metals have long been known to re- duce certatn aromatic systems to their dihydro product . In many cases the reduction proceeds even further to more saturated products. 'I'his medium has also served ,to c1ea1le-var-ioui?-rneleeules-.-'----------- The first reported use of this reaction was by Lebeau and Picon (1) in 1914 whereby naphthalene was reduced to tetrahydronaphthalene. During the nineteenth centuvy similar reductions had been done with sodium amalgam and water ( 2) . Dur:i.ng the several decades following the discovery of these reactions, several reaction mechanisms were proposed (3). The first envolved the reaction of the alkali metal with the ammonia to produce "nascent" hydrogen which then reacted with the hydrocarbon. This is given by equations 1 and 2. This "nascent" hydrogen, (H)*, was . 4Na + 4NH ~ 4NaNH + 4 (H)* 1 3 2 !i(H)* + ClOH8---? Cl0Hl2 2 rather vaguely referred to as a chemically distinct species of hydrogen which preferentially reduced aromatic hydrocarbons rather thaYl I combined to form hydrogen molecules ( 16). The second mechanism mvolved addition of the alkali metal to -- "" the naphthalene followed by solvolysis to the reduced hydrocarbon. This is g1 ven by equations 3 and 4. This particu1ar mechanism was supported by the isolation of 1,1! dilithium naphthalene I (4), .2 c1d1s + 4Na --7 c10H8Na4 3 c H Na + 4NH ~ c H + 4NaNH 4 10 8 4 3 10 12 2 a possible intermed~ate. As further support for thi.s mechanism,· I is was shown that the tetrahydro product was formed stepwise (5), · 2N'a + 2NaNH ? 2 5 2Na Na E-(-- A third theory proposed that the intermediate in the reaction was an anionic species derived from the hydrocarbon ( 5) • For naph- thalene the cJianion III was proposed. Whether the electrons added III 3 directly from the ammonia solution to the naphthalene or whether II formed and then ionized to III was not known. · Since benzene and its simple homologs generally do not add alkali metals, benzene or toluene was often used as a cosolvent for the reduction of large polynuclear aromatic systems of low solubility in ammonia. In 1937 Wooster (6) showed that toluene could also react under these conditions if water were present. Although the products he obtained were not characterized, it was shown_tha.t_wat:er>.____ ______ . must be pi>esent for ring reduction and that anhydrous ammonia with ammonium chloride, ethyl bromide, or iron oxides yielded only molec- ular hydrogen and unreacted toluene. This initiated more interest in the "nascent" hydrogen theory as a possible mechanism for these reactions. Later vlooster improved his methods ('"() for reducing the mono- benzenoid systems by using alcohols as proton sources rather than water. This provided the first easy way to reduce monobenzenoid compounds to their dihydro products. The reaction as reported by Wooster, along with many modifications, is generally referred to as the Birch reduction, stemming from the numerous reports by Birch and his co-workers on this reaction (8-15). Due to the fact that alkali metals do not normally add to mono- benzenoid systems, the mechanisms applicable to polynuclear aromatics, i.e. the addition of the metal followed by solvolysis, were considered untenable for these systems.
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