Structures of pyridines obtained in the aluminum bromide mediated cyclocongregation of acetylenes with cyanoformates

R Wedinger, H Hogeveen…

Index: Wedinger, R.; Hogeveen, H.; Noble, W. J. le Journal of Organic Chemistry, 1984 , vol. 49, p. 1338 - 1341

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Citation Number: 5

Abstract

It is shown that the product of the title reaction with tert-butylacetylene and ethyl cyanoformate is not ethyl 3, 5-di-tert-butyl-2-picolinate as reported in the recent literature but rather the 4, 5-isomer. Varying yields of the 4, 6-isomer are also obtained. The NMR spectra described for the 3, 5-dimethyl analogue likewise suggest a misassignment of structure in that case. A revised mechanism is tentatively given for these reactions.