The reaction of isobutyrophenone phenylhydrazone or 3-phenyl-2-butanone phenylhydrazone with polyphosphoric acid gave an equilibrium mixture of 3,3-dimethyl-2-phenyl-3//-indole and 2,3-dimethyl-3-phenyl-3//-indole contrary to previous reports. The preparation of the 3//-indoles from the phenylhvdrazones can be accomplished without equilibration in acetic acid. Some features of the equilibration have been investigated. The spectroscopic properties of the 3//-indoles are re-
The reaction of thiols with 2,3-epoxides of bicyclo, conjugated 1,4-diketones was found to proceed readily to give the dehydrated thio-substituted enediones or their enolized isomers, depending upon the reaction conditions and the bicyclic bridging of the starting materials. In no case was a mixture of these isomers observed. Enediones generally resulted from these reactions with and without triethylamine catalysis, whereas the use of an equimolar amount of triethylamine generally gave hydroquinones. The ease of rearrangement of enedione to hydroquinone followed the order: 2,3-dimethylbutadiene adduct [Formula: see text] reduced cyclopentadiene adduct > cyclopentadiene adduct = 1,3-cyclohexadiene adduct.
Twenty-five grams (0.15 mole) of XIV was refluxed with 42 g. of sodium hydroxide, dissolved in 350 ml. of water, for 24 hours. During this time ammonia was given off. The solution was then acidified with concentrated hydrochloric acid and refluxed for five hours more.The mixture was then filtered and extracted three times with ether, dried and distilled to yield 8 g. of -ethoxy-Y-valerolactone, b.p. 127-129°( 14 mm.), »26d 1.4419, yield 36%.
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