Mechanism of the Formation of Tetraphenyl-Lead from Lead Chloride and Phenyllithium

The present study is concerned with the formation of tetraphenyllead from lead chloride and phenyllithium. It is probable that the closely related phenyllithium and phenylmagnesium bromide react with lead chloride by closely related mechanisms. By using, at this time, phenyllithium in place of phenylmagnesium bromide, we were able to avoid possible secondary reactions involving magnesious bromide and magnesium bromide

n-Octadecylamine and Di-n-Octadecylamine and Their derivatives

n-Octadecylamine and di-n-octadecylamine have been prepared by various methods, and particularly by both the wet and the catalytic reduction of stearonitrile. The report includes a study of new derivatives (some useful for purposes of characterization), and rearrangement reactions

High Molecular Weight, Normal and Branched Aliphatic Compounds

A series of high molecular weight compounds (hydrocarbons, alcohols, amines, etc.) is being examined for correlations between molecular weight and viscosity. In some of the syntheses (particularly those of hydrocarbons, alcohols and ketones) long-chained aliphatic organometallic compounds have been used. Some of these have been prepared in adequate yields for the first time

Pyridine and Quinoline Derivates of Dibenzofuran, and Their Physiological Properties

A study is in progress of the physiological properties, particularly the narcotic action, of amino and substituted aminodibenzofurans and their nuclear reduction products. The amino compounds in many cases are cyclicized to give pyridino-dibenzofurans. Simple illustrations of parent types are the quinolines derived by Shraup and other syntheses from the amino dibenzofurans and their reduction products. The nitrogen cycles have been extended to include bridging of rings which vary both in kind and position of substituents as well as in degree of nuclear reduction

Morphine Alkaloids and Synthetic Dibenzofuran Derivatives

A continuation of studies patterning synthetic types after morphine alkaloids has now made possible the introduction of substituents into the critical 1-, 4-, 6- and 9-positions. The present report is concerned with methoxy and hydroxy groups in the 4- and 6-positions, and suitably substituted amino groups in the 1-position. A typical compound is 1-(α-aminoethyl )-4-methoxydibenzofuran hydrochloride (m. p., 268-269°), prepared from the oxime of l-acetyl-4-methoxydibcnzofuran by conventional reactions. So far success has not attended several attempts to bridge the 1- and 9-positions. Where cyclization does take place it goes homonuclearly and not heteronuclearly. It is possible that di-cyclization may proceed easier by first bridging the 1- and 9-positions, and then effecting an oxygen-bridge

Trialkylgold Compounds

Evidence has been found for the existence of trialkylgold compounds. They may be prepared by the action of the alkyllithium derivatives on the corresponding dialkylgold halides

The Friedel-Crafts Reaction with Long-Chained Alkyl Bromides (Abstract)

It has been reported that 1-bromooctadecane reacts with benzene 1md aluminum chloride to give a 50 per cent yield of 1-phenyloctadecane. [Gilman and Turck, J. A. Chem. Soc., 61, 478 (1939) J. We have found that 1-bromohexadeeane, 1-bromotetradecane and 1-bromododecane behave similarly. The case of 1-bromododecane was studied in more detail. Evidence was found that, in addition to 1-phenyldodecane, isomeric dodecylbenzenes were formed. Incidental to this work the six isomeric 2-naphthalene-sulfono-pn-dodecylanilides (B-C10H7.SO2.NH.C6H4.C12H25) were prepared for use in a study of the validity of the mixed melting point determinations with structurally similar long-chained compounds. Fractionation of the\u27 products of the reaction of 1-bromohexane, benzene and aluminum chloride (carried out at 0°) showed that 1-phenylhexane, 2-phenylhexanc and 3-phenylhexane were obtained. These hydrocarbons were characterized as their monacetamino and diacetamino derivatives [Ipatieff and Schmerling, ibid, 59, 1056 (1937) and as the sulfonamides. They were identified by comparison with synthetic specimens

Furan Arsenicals

Furan arsenicals can be prepared by the interaction of furan mercurials and arsenic chloride. The reaction is capable of extensive application because of the availability of a miscellany of furan mercurials having the murcuri group both in the alpha- and beta positions. Another method involves the interaction of recently accessible furan Grignard reagents with arsenic halides

High Molecular Weight Fatty Acid Derivatives

A series of derivatives for identifying lauric, myristic, palmitic, stearic and oleic acids have been prepared. The ten best series of derivatives may be listed in the following order of decreasing importance: (1) N-acylcarbazole derivatives; (2) N-acyl-p-toluenesulfonamides; (3) p-phenyl-phenacyl esters; (4) N-acylphenothiazine derivatives; (5) N-acyl-2-nitro-p-toluidine derivatives; (6) N-acylsaccharin derivatives; (7) 2, 4-dinitrophenylhydrazides; (8) p-nitro-anilides; (9) phenylmercuric salts; (10) p-xenylamides

Some Rearrangement Reactions of Organosodium and Organolithium Compounds

In continuation of rearrangement reactions of organometallic compounds, it was desirable to ascertain whether R-Metal combinations (free of halogen or other acidic groups) would react after the manner of benzylmagnesium chloride types with compounds like formaldehyde, for example. This last reaction gives not only the normal product (beta-phenylethyl alcohol), but also o-tolyl carbinol. It has been shown that the corresponding organosodium and organolithium compounds behave in a similar manner. Incidentally, it is possible to prepare some organolithium compounds, like phenyl-lithium, very conveniently, in a short time, and in excellent yields in the customary three-necked flasks