Synthesis of two new gem-fluoronitro contained tetranitroadamantanes and property comparison with their nitro and gem-dinitro analogues

摘要

Two new fluorinated tetranitroadamantanes, 2,6-difluoro-2,4,4,6-tetranitroadamantane and 2,4,6,8-tetrafluoro-2,4,6,8-tetranitroadamantane, were synthesized. 2,6-Difluoro-2,4,4,6-tetranitroadamantane was prepared from 4,4-dinitroadamantane-2,6-dione by a three-step route with an overall yield of 40%. It has a slightly higher crystal density (1.787 g cm~(-3)) than its analogue 2,2,4,4,6,6-tetranitroadamantane (1.777 g cm~(-3)). 2,4,6,8-Tetrafluoro-2,4,6,8-tetranitroadamantane was prepared from 4,8-dihydroxyadamantane-2,6-dione by an eight-step route with an overall yield of 8%. It is notable that the replacement of one nitro group in gem-dinitro functonality with flluorine might slightly reduce the detonation performance but improve the density and inherent steric hindrance, which makes possibility for introducing more nitro functionalities on the adamantane backbone.