Reactivity Investigation of Bis-Tetrazole Isomers Prepared through Dimroth Rearrangement

Xiangyan Miao; Jiyuan Yu; Shuaijie Jiang; Yuchuan Li; Siping Pang

doi:10.1021/acs.orglett.5c04729

Reactivity Investigation of Bis-Tetrazole Isomers Prepared through Dimroth Rearrangement

Xiangyan Miao
, Jiyuan Yu
, Shuaijie Jiang
, Yuchuan Li^*
, Siping Pang^*

^*此作品的通讯作者

Beijing Institute of Technology
Nanjing University of Science and Technology

科研成果: 期刊稿件 › 快报 › 同行评审

1 引用（Scopus）

摘要

The synthesis of two isomeric compounds, 2 and 3, was achieved from 1 through a one-step Dimroth rearrangement. By exploiting the distinct reactivity of these isomeric precursors under identical reaction conditions, we successfully synthesized high-nitrogen content compounds 4–6. ELF-π analysis and DFT calculations reveal that the amino group in compounds 4 and 5 enhances electron delocalization, demonstrating how positional isomerism can guide the design of high-performance high-density energetic materials (HEDMs).

源语言	英语
页（从-至）	929-934
页数	6
期刊	Organic Letters
卷	28
期	3
DOI	https://doi.org/10.1021/acs.orglett.5c04729
出版状态	已出版 - 23 1月 2026
已对外发布	是

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title = "Reactivity Investigation of Bis-Tetrazole Isomers Prepared through Dimroth Rearrangement",

abstract = "The synthesis of two isomeric compounds, 2 and 3, was achieved from 1 through a one-step Dimroth rearrangement. By exploiting the distinct reactivity of these isomeric precursors under identical reaction conditions, we successfully synthesized high-nitrogen content compounds 4–6. ELF-π analysis and DFT calculations reveal that the amino group in compounds 4 and 5 enhances electron delocalization, demonstrating how positional isomerism can guide the design of high-performance high-density energetic materials (HEDMs).",

author = "Xiangyan Miao and Jiyuan Yu and Shuaijie Jiang and Yuchuan Li and Siping Pang",

note = "Publisher Copyright: {\textcopyright} 2025 American Chemical Society",

year = "2026",

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doi = "10.1021/acs.orglett.5c04729",

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TY - JOUR

T1 - Reactivity Investigation of Bis-Tetrazole Isomers Prepared through Dimroth Rearrangement

AU - Miao, Xiangyan

AU - Yu, Jiyuan

AU - Jiang, Shuaijie

AU - Li, Yuchuan

AU - Pang, Siping

PY - 2026/1/23

Y1 - 2026/1/23

N2 - The synthesis of two isomeric compounds, 2 and 3, was achieved from 1 through a one-step Dimroth rearrangement. By exploiting the distinct reactivity of these isomeric precursors under identical reaction conditions, we successfully synthesized high-nitrogen content compounds 4–6. ELF-π analysis and DFT calculations reveal that the amino group in compounds 4 and 5 enhances electron delocalization, demonstrating how positional isomerism can guide the design of high-performance high-density energetic materials (HEDMs).

AB - The synthesis of two isomeric compounds, 2 and 3, was achieved from 1 through a one-step Dimroth rearrangement. By exploiting the distinct reactivity of these isomeric precursors under identical reaction conditions, we successfully synthesized high-nitrogen content compounds 4–6. ELF-π analysis and DFT calculations reveal that the amino group in compounds 4 and 5 enhances electron delocalization, demonstrating how positional isomerism can guide the design of high-performance high-density energetic materials (HEDMs).

UR - https://www.scopus.com/pages/publications/105028337296

U2 - 10.1021/acs.orglett.5c04729

DO - 10.1021/acs.orglett.5c04729

M3 - Letter

C2 - 41460307

AN - SCOPUS:105028337296

SN - 1523-7060

VL - 28

SP - 929

EP - 934

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Reactivity Investigation of Bis-Tetrazole Isomers Prepared through Dimroth Rearrangement

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