Construction of an All-Bridge Carbon-Oxidized 2-Azaadamantane Skeleton and Synthesis of Two Energetic Derivatives
The construction of an all-bridge-oxygenated (hetero)adamantane skeleton is a long-standing challenge. Herein, an all-bridge carbon-oxidized 2-azaadamantane skeleton, 6,9,10-trimethoxy-2-azaadamantane-4,8-diol, was constructed via an eight-step synthetic route from 9-hydroxybicyclo[3.3.1]nonane-2,6-dione with an overall yield of 45%. The obtained skeleton was derived into two novel high-performance energetic compounds. Among them, 2,9,9,10,10-pentanitro-2-azaadamantane-4,6,8-triyl trinitrate is the first example that possesses eight explosophoric groups on the adamantane skeleton.
Authors
- Yunzhi Liu (ORCID: https://orcid.org/0000-0003-0524-4023)
- Jun Luo (ORCID: https://orcid.org/0000-0002-8093-5345)
- Long Zhu (ORCID: https://orcid.org/0000-0002-1850-6427)
- Huan Li (ORCID: https://orcid.org/0000-0002-3501-298X)
- Yu Zhang (ORCID: https://orcid.org/0000-0003-3492-727X)
- Bing Li (ORCID: https://orcid.org/0000-0001-5363-7070)
- Guixiang Wang (ORCID: https://orcid.org/0000-0002-7404-0131)
- Qi Zhou (ORCID: https://orcid.org/0000-0001-7237-4659)
Institutions
- Nanjing University of Science and Technology (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-24
- DOI
- https://doi.org/10.1021/acs.orglett.5c00447
- Citations
- 7
- Primary Topic
- Chemical Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 6.55
Funders
- National Natural Science Foundation of China