K 2 S 2 O 8 -mediated nitration of alkenes with NaNO 2 and 2,2,6,6-tetramethylpiperidine-1-oxyl: stereoselective synthesis of ( E )-nitroalkenes
Zhao An
1
,
Jiang Qing
1
,
Jing Jia
1
,
Bin Xu
1
,
Yu Feng Liu
1
,
Ming Zhong Zhang
1
,
Qiang Liu
1
,
Weiping Luo
1
,
Cancheng Guo
1
Publication type: Journal Article
Publication date: 2016-01-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A transition-metal-free nitration of alkenes with NaNO2 in the presence of K2S2O8 and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) is developed. The transformation exhibits a broad substrate scope and good functional group tolerance, thus providing a new and expedient protocol for stereoselective synthesis of (E)-nitroalkenes with moderate to good yields. Moreover, the nitration processes of (E)- and (Z)-stilbene are also studied: even though the proportion of substrates is different, the E/Z ratio of the products is basically the same. Based upon experimental observations, a possible reaction mechanism is proposed.
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35
Total citations:
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Citations from 2025:
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(5.71%)
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GOST
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An Z. et al. K 2 S 2 O 8 -mediated nitration of alkenes with NaNO 2 and 2,2,6,6-tetramethylpiperidine-1-oxyl: stereoselective synthesis of ( E )-nitroalkenes // Tetrahedron Letters. 2016. Vol. 57. No. 1. pp. 80-84.
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An Z., Qing J., Jia J., Xu B., Liu Yu. F., Zhang M. Z., Liu Q., Luo W., Guo C. K 2 S 2 O 8 -mediated nitration of alkenes with NaNO 2 and 2,2,6,6-tetramethylpiperidine-1-oxyl: stereoselective synthesis of ( E )-nitroalkenes // Tetrahedron Letters. 2016. Vol. 57. No. 1. pp. 80-84.
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TY - JOUR
DO - 10.1016/j.tetlet.2015.11.064
UR - https://linkinghub.elsevier.com/retrieve/pii/S0040403915303713
TI - K 2 S 2 O 8 -mediated nitration of alkenes with NaNO 2 and 2,2,6,6-tetramethylpiperidine-1-oxyl: stereoselective synthesis of ( E )-nitroalkenes
T2 - Tetrahedron Letters
AU - An, Zhao
AU - Qing, Jiang
AU - Jia, Jing
AU - Xu, Bin
AU - Liu, Yu Feng
AU - Zhang, Ming Zhong
AU - Liu, Qiang
AU - Luo, Weiping
AU - Guo, Cancheng
PY - 2016
DA - 2016/01/01
PB - Elsevier
SP - 80-84
IS - 1
VL - 57
SN - 0040-4039
SN - 1873-3581
ER -
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@article{2016_An,
author = {Zhao An and Jiang Qing and Jing Jia and Bin Xu and Yu Feng Liu and Ming Zhong Zhang and Qiang Liu and Weiping Luo and Cancheng Guo},
title = {K 2 S 2 O 8 -mediated nitration of alkenes with NaNO 2 and 2,2,6,6-tetramethylpiperidine-1-oxyl: stereoselective synthesis of ( E )-nitroalkenes},
journal = {Tetrahedron Letters},
year = {2016},
volume = {57},
publisher = {Elsevier},
month = {jan},
url = {https://linkinghub.elsevier.com/retrieve/pii/S0040403915303713},
number = {1},
pages = {80--84},
doi = {10.1016/j.tetlet.2015.11.064}
}
Cite this
MLA
Copy
An, Zhao, et al. “K 2 S 2 O 8 -mediated nitration of alkenes with NaNO 2 and 2,2,6,6-tetramethylpiperidine-1-oxyl: stereoselective synthesis of ( E )-nitroalkenes.” Tetrahedron Letters, vol. 57, no. 1, Jan. 2016, pp. 80-84. https://linkinghub.elsevier.com/retrieve/pii/S0040403915303713.