Polyfluorocycloalkenes. Part X. Replacement reactions of octafluorocyclohexa-1,3- and -1,4-diene

Abstract

Octafluorocyclohexa-1,3-diene and methyl-lithium in ether gave 1-, 2-, and 5-methylheptafluorocyclohexa-1,3-diene and 3-methylheptafluorocyclohexa-1,4-diene in the approximate ratio of 2 : 90 : 1 : 3, respectively; with methanolic potassium hydroxide it gave 1- and 2-methoxyheptafluorocyclohexa-1,3-diene and 3-methoxyheptafluorocyclohexa-1,4-diene in the approximate ratio of 1 : 12 : 2, respectively. Octafluorocyclohexa-1,4-diene and methyl-lithium in ether gave 1- and 3-methylheptafluorocyclohexa-1,4-diene in the ratio of 38 : 1; with methanolic potassium hydroxide it gave 1-methoxyheptafluorocyclohexa-1,4-diene and a 4H-5-methoxyoctafluorocyclohexene. In the characterisation of these substitution products, 2-methyl- and 2-methoxy-heptafluorocyclohexa-1,3-diene have been synthesised by unequivocal routes based on 1-methyl- and 1-methoxy-nonafluorocyclohexene.