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Organic Seminar Abstracts LIB RA R.Y OF THE UN 1VERSITY or 1 LLI NOIS Q.541 pt.l Return this book on or before the Latest Date stamped below. Theft, mutilation, and underlining of books are reasons for disciplinary action and may result in dismissal from the University. University of Illinois Library L161— O-1096 Digitized by the Internet Archive in 2012 with funding from University of Illinois Urbana-Champaign http://archive.org/details/organicsemi1962631univ ORGANIC SEMINAR ABSTRACTS I962-I963 IVERSITY OF ILLINOIS LIBRARY Paging varies but this is complete. Department of Chemistry and Chemical Engineering University of Illinois ORGANIC SEMIHAR ABSTRACTS 1962-1963 Semester I Department of Chemistry and Chemical Engineering University of Illinois SEMINAR TOPICS I Semester 1962-I963 Introduction of Functionality in the Angular Position of Fused Ring; Systems G. E. Wilson, Jr 1 Dinitrocyclohexanes Philip C. Kelley ......... 7 it -Complexes of Transition Metals with Mono-olefins M. P. Dixon 16 Structural Studies of Macrocyclic Pentaene Antibiotics G. Leadbeiter ...... Recent Applications of the Wittig Reaction H. E. Dunn . 33 Chemistry of Cyclic Azo Compounds T. II. Fisher ho The Mechanism of the Benzidine Rearrangement Richard A. Laursen . k-S) Conformational Studies of Five-membered Rings R. L. Buckson 58 Structure of Catalposide Walter J. Musliner 67 Recent Investigations on Morphine and Related Compounds Richard F, Schimbor 7^- The Biosynthesis of Branched Chain Fatty Acids W. P. O'Neill G3 The Photolysis of Diazoketones T. M. Warne 92 Nuclear Magnetic Double Resonance John P. Petrovich ........ 100 Stereochemistry, Synthesis and Biogenesis of Tropanes Richard K. Olsen 109 cis -trans Isomerization Mechanisms in Acid Solution L. Miller 118 The Mechanism of Oxymercuration and Deoxymercuration W. G. DeWitt 125 Long-range Nuclear Spin-spin Coupling W. Ripka „ 1 I Diimide Chemistry John F. Coleman ll+3 The Ferri examines Clifford H. Cox ..... 152 INTRODUCTION OF FUNCTIONALITY IN THE ANGLULAR POSITION OF FUSED RING SYSTEMS Reported by G. E. Wilson, Jr. September 17, 19^2 The presence of the angular methyl group with specific stereochemistry in natural products such as steroids (l) is well known. Consequently considerable time has been spent in the development of methods for methylating the angular position in a stereoselective manner. This interest has led to the development of methods for introduction of functional- ity other than methyl groups both for modification of existing structures and for synthesis of new compounds. This seminar will be concerned with reactions which introduce one-carbon fractions: (a) methylation of enolate anions, (b) nucleophilic additions to a, p -unsaturated carbonyl groups, and (c) miscellaneous reactions introducing only one angular carbon atom. The last subdivision will be treated first. Miscellaneous reactions introducing one angular carbon atom Most reactions of this type are of limited utility due to the stringent qualifications to be met by functional groups already on the existing structure. The Reimer-Tiemann reaction has been applied to 5>6>7,8-tetrahydro-2-naphthol (i) to obtain 10-dichloromethyl- 1 ' 9 ' 3 2-keto-A -hexahydronaphthalene (2). This was reduced and hydrogenolyzed in alcoholic potassium hydroxide to 10-methyl-2-decalol, (II), stereochemistry unknown. Corey used a biogenetic-type cationic addition to a double bond to form a ring with two stereospecific angular methyl groups in the synthesis of a p-amyrin derivative (V)(3)» Similar cyclizations have been reported by Barton (k) , Corey (5) and others. Simultaneously Chuang (6) and Cook and Lawrence (7) found that 9 -methyl -1-decalone can be made by catalytic reduction of the product of cyclization of 4-(2-methylhexenyl)butryl chloride with stannic chloride. HC1 HOAc Many syntheses in the steroid field have involved cyclization of a five- or six-mem- bered'ring thereby creating an angular methyl group. The use of the Dieckmann reaction to elaborate the D ring of steroids was used extensively by Bachmann (8,9). Little steric control is possible in these reactions. The general scheme is illustrated below. COOMe l)Zn,BrCHPCHpC00Me 2) S0C12 .CHaL^ COOMe NaOMe 3) KOH /-\pC00H k) Na(Hg) ^k>\^00K 00 Me 2 isomers 1) NaOMe ~2) H + Arndt-Eistert COOMe 3 Methylation of enolate anions The product of the methylation of the angular position should contain a predominance of the trans fused ring system;, it is this system which occurs widely in natural steroids and terpenes. Because the introduction of an angular methyl group in the 1-decalone system shifts the equilibrium from 95$ to k(tf> trans ring fusion (10,, one reasons that the method must proceed with kinetic control. Application late in the synthesis of a natural product makes it imperative that the yields be high and. conditions mild. In the 1-decalone system the enolate may be formed on either side of the ketone. Cook and Lawrence found that treatment of 1-decalone with sodamide and methyl iodide gave 2- methyl-1-decalone and a trace of 9-methyl-l-decalone (7). Isolated cases, all with the keto group in the B or C ring of a steroid, gave the angularly methylated compounds as the main - -2- products. Peak and Robinson obtained angularly methylated compounds from the reaction of 12-ketosteroids with potassium t~butoxide and methyl iodide (ll). More recently Fried and Arth treated the 6-ketosteroid (VI) With sodium hydride and methyl iodide in refluxing xylene to obtain the 5£-product, having a eis a/b ring fusion, in 37 per cent yield (12). NaH, Mel xylene Blocking groups for the methylation of enolate anions A blocking group is used in the 2-position of a 1-decalone to assure that alkylation will occur at the angular position. The requirements for such a group are that it must be easily introduced, inert to the conditions for methylation, and easily removed. Only compounds derived from aldehyde condensations with a 1-decalone have met these conditions. Aryl aldehydes and furfuraldehyde lead to the arylidene and the furfurylidene derivatives respectively. Hie reaction with ethyl formate and sodium °H.ves the 2-hydroxymethylene reacts either purification with amines, derivatives which in situ or _ after thiols, and aj_kyi halides to yield the useful aminomethylene, thiomethylene and alkoxymethyl- ene derivatives. The first use of a blocking group to direct methylation was reported by Robinson who methylated the piperonylidene derivative of the methyl ether of l8-norequilenin (lj). No cleavage of the blocking group was tried immediately. The first derivative of a 2-hydroxymethylene -1-decalone investigated was the methyl -- anilinomethylene derivative. Condensing a 1-decalone with ethyl formate and sodium formed the 2-hydroxymethylene compound. Reaction of this with N-methylaniline gave the desired derivative (14). Cleavage after methylation was easily accomplished by hydrolysis. The pyrrolidinomethylene blocking group, synthesized in much the same manner, has the disadvantage of deactivating the ketone to methylation (14,15). Johnson investigated the use of 2 -alkoxymethylene derivatives as blocking groups (i6). These were formed by heating a 2-hydroxymethylene-l-decalone with an alkyl halide and potassium carbonate in acetone. When the a,lkyl halide was methyl iodide the yield of enol ether was only 20 per cent, the rest of the material being the product of C-alkylation. The isopropoxymethylene derivative was easily synthesized in high yield and was not so easily hydrolyzed as the methoxymethylene derivative. Cleavage of the enol ether after the methylation reaction was accomplished by treating it with ethanolic ferric chloride solution. The resultant hydroxymethylene derivative was then liberated from the iron complex by dilute acid and cleaved by alkaline hydrolysis. The chief disadvantages of this derivative are its sensitivity to water and to the methylating conditions. Ireland and Marshall introduced the n-butylthiomethylene blocking group (17,18). This group utilizes to advantage the high electronegativity of the sulfur atom and its inability to participate in resonance. This derivative can be synthesized by two methods. The 2- hydroxymethylene-1-decalone can be refluxed with n-butyl mercaptan and a trace of p_-toluene sulfonic acid, using benzene to remove water in the azeotrope. For acid labile compounds the tosylmethylene derivative is made from the hydroxymethylene compound in the usual manner. Addition of the mercaptan to this mixture yields the alkylthiomethylene derivative. The alkylthiomethylene group is acid labile; but it is most conveniently removed by aqueous sodium hydroxide in diethylene glycol. Reductive desulfurization leaves a 2, 9 -dimethyl -1- decalol (19). Condensation of benzaldehyde with 1-decalone in 10 per cent sodium hydroxide solution introduced the 2-benzylidene blocking group (20). Methylation of this substance with potassium t-butoxide and methyl iodide proceeded in 91 per cent yield. The blocking group can be removed by the following series of reactions without the intermediate isolation of . M . -3- products: Chlorination in carbon tetrachloride is followed by treatment with sodium methoxide to form the enol ether . Hydrolysis to the diketone is followed by cleavage to the monoketone with dilute base. Alkaline cleavage can proceed in either direction so that yields are sometimes low. When this procedure was used by Birch, Jaeger and Robinson for removal of the piperonylidene group from the aromatic steroid VIII, chlorination of the aromatic ring occurred before chlorination of the double bond (21). CI 'la(xs) VIII CC1, Johnson has described the methylation of 2-p_-methoxybenzylidene- 2-p_-chlorobenzyiidene7 2-p_-dimethylaminoben3ylidene-5 2-£-nitrobensylidene-j 2-a-naphthaylmethylene-and 2 -furfuryli- dene-1-decalones (20, 22). In all cases the cis fused ring system predominated when methylated. Steric control in the methylation of enolate anions Before any significant work can be done on steric control of methylation, a method, must exist for interpreting and measuring results. Early work suggested that methylated cis fused 2-arylmethylene-l-decalones absorbed at longer wavelength in the ultraviolet.
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