Difluoramination of a tetrahydro-1,5-diazocine-3,7(2H, 6H)-dione to the corresponding 3,3,7,7-tetrakis(difluoramino)diazocine was achieved by a judicious choice of protecting group. Arenesulfonyl protecting groups for the diazocine nitrogens proved superior to acetyl during the slow disruption of the transannular bridge in 9-oxa-3,7-diazabicyclo[3.3.1]nonane intermediates by difluorosulfamic acid, While a 1,5-ditosyl derivative failed to proceed beyond the product of addition of difluoramine to one ketone carbonyl (hemiaminal 6), the use of 4-nitrobenzenesulfonyl as the protecting groups lowered the nitrogens' basicities below that of the oxygen site in the dione and intermediates, allowing the reaction to proceed to a gem-bis(difluoramino)diazocine product (11). A safer procedure for handling difluoramine is described.