Formation of bicyclic adducts in the reactions of fluorinated 2,4-cyclohexadien-1-ones with 2-carboxyhenzenediazonium

Benzyne generated during the decomposition of 2-carboxybenzenediazonium interacts with 6-chloro-2,3,4,5,6-pentafluoro-2,4-cyclohexadien-1-one, 6-chloro-2,4,5,6-tetrafluoro-3-methoxy-2,4-cyclohexadien-1-one, 6-chloro-2,4,5,6-tetrafluoro-3-(pentafluorophenoxy)-2,4-cyclohexadien-1-one, and perfluoro-6-phenoxy-2,4-cyclohexadien-1-one to form [4+2]-cycloaddition products. The latter are easily converted to 1-naphthylacetic acid derivatives by the action of O- and N-nucleophiles.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1634–1637, September, 1994.This work was carried out with the financial support of the International Science Foundation (Project No. Ch₂-6713-0925).