Graduate Thesis Or Dissertation

 

The preparation and reactions of 1-(2-pyridyl)-3-menthyl-3-butene-2-ol and 1-(2-pyridyl)-4-methyl-3-butene-2-ol Public Deposited

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  • 1-(2-pyridyl)-3-methyl-3-butene-2-ol was prepared by allowing 2-picolyllithium to react with methacrolein. In the reaction of picolyllithium with crotonaldehyde, two products 1-(2-pyridyl)-4-methyl-3-butene-2-ol and 1-(2-pyridyl)-4-methyl-2-butene-4-ol were formed. 1-(2-pyridyl)-3-methyl-3-butene-2-ol was subjected to the low pressure hydrogenation, using methanol as solvent and PtO₂ as catalyst. A red yellow liquid 1-(2-pyridyl)-3-methyl-2-butanol was obtained. Derivatives of the alcohol were prepared and a structure assigned. 2-hydroxy-3-methyl-3-bromo-1, 2, 3, 4-tetrahydroquinolizinium bromide was formed when bromine was added, in carbon tetrachloride, to 1-(2-pyridyl)-3-methyl-3-butene-2-ol. 2-hydroxy-3-bromo-3-methyl quinolizidine hydrogen bromide was obtained when 2-hydroxy-3-methyl-3-bromo-1, 2, 3, 4-tetrahydroquinolizinium bromide was subjected to low pressure hydrogenation. 2-hydroxy-3-bromo-4-methyl-1, 2, 3, 4-tetrahydroquinolizinium bromide and 2-hydroxy-3-iodo-4-methyl-1, 2, 3, 4-tetrahydroquinolizinium iodide were also obtained when treated 1-(2-pyridyl)-4-methyl -3-butene-2-ol with bromine and iodine in carbon tetrachloride. The benzoate and the acetate of 1-(2-pyridyl)-4-methyl-3-butene-2-ol were formed when treated with benzoyl chloride and acetyl chloride. The refactive index of each liquid was measured. The I. R. and U. V. spectra of the compounds was determined.
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