Issue 26, 2018

Synthesis of two new gem-fluoronitro containing 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 the gem-dinitro functionality with fluorine might slightly reduce the detonation performance but improve the density and inherent steric hindrance, which makes it possible to introduce more nitro functionalities on the adamantane backbone.

Graphical abstract: Synthesis of two new gem-fluoronitro containing tetranitroadamantanes and property comparison with their nitro and gem-dinitro analogues

Supplementary files

Article information

Article type
Communication
Submitted
15 میٔ 2018
Accepted
10 جوٗن 2018
First published
12 جوٗن 2018

Org. Biomol. Chem., 2018,16, 4784-4788

Synthesis of two new gem-fluoronitro containing 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, 16, 4784 DOI: 10.1039/C8OB01140K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements