Organic Lab Reactions 244

Organic Lab Reactions 244 - is obtained. 24 COOH Ring...

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REACTION OF DIAZONIUM SALTS 239 From dry solid benzenediazonium chloride, benzene, and aluminum chloride, biphenyl is obtained in 33% yield. •N 2 +C1- + HC1 Similar reactions have been carried out with naphthalene and thiophene. The method has been employed only to a limited extent 23 since its dis- covery, probably because it involves the isolation of the dry diazonium salts and because a number of aryldiazonium salts (from o- and p- toluidine and /3-naphthylamine) gave no biaryls but only the corre- sponding aryl halides. Pschorr Synthesis. In this synthesis of phenanthrene derivatives, one of the steps involves the union of two aryl nuclei through a diazotiza- tion reaction. By treatment of diazotized a-phenyl-o-aminocinnamic acid with copper, 9-phenanthroic acid
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Unformatted text preview: is obtained. 24 COOH Ring closure of m-o-aminostilbene (XIX) to phenanthrene, o-aminobi-benzyl (XX) to 9,10-dihydrophenanthrene, and o-aminodiphenylmeth-ane (XXI) to fluorene can be effected likewise through the diazonium reaction. 25 A number of substituted fluorenones have been prepared by this method. 2Ba CH=CH • XXI Reaction of Diazonium Salts with Quinones and with Phenols. Aryl-diazonium salts couple with quinones in the presence of sodium acetate to " Knowles, J. Am. Chem. Soc., 43, 896 (1921). 24 See Johnson, Org. Reactions, I, 246 (1942). u See Kornblum, Org. Reactions, this volume. . ••• Lothrop and Goodwin, J. Am. Chem. Soc., 66, 363 (1943)....
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This note was uploaded on 11/20/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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