Reactions of I-(α-pyridyl)-3-buten-1-o1 Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/c821gp829

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  • The purpose of this project was to study the reactions of 1-(α-pyridyl)-3-buten-1-ol (compound I) and to determine whether or not the products of some of its reactions are quinolizinium salts. Reaction of compound I with bromine or iodine yields halide salts (when no external cooling is applied) instead of the expected dihalides. The identification of these salts has not been positively established, however, it has been suggested that they are quinolizinium salts directly analogous to those prepared by Wischmann. The failure to positively identify these salts is primarily three-fold: 1) no N. M. R. identification has yet been made, 2) identification of some of the important I. R. bands has not been established due to confusion in the literature, 3) different products may be isolated from a given reaction by varying the conditions of reaction and/or isolation. A comparison of the I. R. spectrum of an authentic quinolizinium salt with the I. R. spectra of these salts indicates that these salts are probably not quinolizinium salts. Compounds prepared in the course of this study were 1-(α-pyridyl)-3-buten-1-ol, its phenyl urethane, 1-(α-pyridyl)-butanol, 1-(α-pyridyl)-3-buten-1-yl acetate, 1-(α-pyridyl)-3-buten-1-yl benzoate, 1-(α-pyridyl)-3-bromobutanol hydrobromide, 1-(a-pyridyl)-4-bromobutanol hydrobromide, 1-(α-pyridyl)-3-bromobutanol, 1-(α-pyridyl)-4-bromobutanol, and the salts obtained by reacting each of the following compounds with bromine and iodine: 1-(α-pyridyl)-3-buten-1-ol, 1-(α-pyridyl)-3-buten-1-yl acetate, and 1-(α-pyridyl)-3-buten-1-yl benzoate. An infrared spectrum was obtained for each product which was prepared in sufficient quantity and which was isolated pure or nearly pure. Melting points of all solids were deterrnined. Boiling points of all liquids were established. Refractive index of each liquid was measured.
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