Reaction with Alcohols of 1-Bromo(chloro)-l,2-epoxyheptafluorobutanes and 1,2-Epoxyperfluorobutane.Preparation of alpha-Bromo-,alpha-Chloro-,and alpha-Alkoxyhexafluorobutyric Acids Esters

摘要

1-Bromo(chloro)-1,2-epoxyheptafluorobutanes reacted with primary and secondary alcohols by two concurrent routes giving a mixture of esters of alpha-alkoxy-and alpha-bromo(chloro)-hexafluorobutyric acids with growing content of the latter on increasing the bulk of the nucleophilic agent.1,2-Epoxyperfluorobutane under the same conditions was converted into alpha-alkoxyhexafluorobutyric acid esters.Reaction of 1-bromo-1,2-epoxyheptafluoro-butane and 1,2-epoxyperfluorobutane with potassium tert-butylate in tert-butanol resulted in tert-butyl alpha-bromohexafluorobutyrate and heptafluorobutyrate respectively due to the forced attack of the bulky nucleophile on the terminal carbon atom of the epoxy ring.