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

Abstract

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.

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Publication details

The article was received on 15 May 2018, accepted on 10 Jun 2018 and first published on 12 Jun 2018


Article type: Communication
DOI: 10.1039/C8OB01140K
Citation: Org. Biomol. Chem., 2018, Accepted Manuscript
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    Synthesis of two new gem-fluoronitro contained tetranitroadamantanes and property comparison with their nitro and gem-dinitro analogues

    J. Zhang, Y. Ling, G. Wang, L. Zhang and J. Luo, Org. Biomol. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8OB01140K

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