Product studies of the photocycloaddition reactions of 5-chloro-and 5-fluorouracil derivatives and olefins. An interesting and useful effect of fluorine on regioselectivity

…, RJ Balchunis, JS Swenton

Index: Wexler, Allan J.; Balchunis, Robert J.; Swenton, John S. Journal of Organic Chemistry, 1984 , vol. 49, p. 2733 - 2738

Full Text: HTML

Citation Number: 11

Abstract

The acetone-sensitized photochemical cycloadditions of 1, 3-dimethyl-5-chlorouracil (la), 5- chlorouracil (lb), 1, 3-dimethyl-5-fluorouracil (4), and 5-fluorouracil (7) have been studied. The 5-chlorouracil systems la and lb gave complex, acidic product mixtures on attempted photocycloaddition to enol acetatea. Only tetramethylethylene underwent clean photocycloaddition with la and lb, affording a mixture of cycloadduct and 1, 3-dimethy1-5-( ...