Nitrolysis of carboxylic t-butyl and 1-adamantyl esters

Article abstract of DOI:10.1016/S0040-4039(98)02079-6

A cheap, less problematic, efficient and selective reagent for the removal of the t-butyl and 1-adamantyl protecting groups from carboxylic esters was found to be commercial 100% HNO₃ in CH₂Cl₂. Incidentally, 1,1- dimethylethyl nitrate and tricyclo[3.3.1.1^3,7]dec-1-yl (1-adamantyl) nitrate are coproducts in a clean reaction. The procedure is in many ways superior to the method employing CF₃COOH.