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（）-2-芳基-1-氰基-1-硝基乙烯与二氮杂芴之间意外的反应过程：为何没有发生1,3-偶极环加成反应？

Unexpected course of reaction between ()-2-aryl-1-cyano-1-nitroethenes and diazafluorene: why is there no 1,3-dipolar cycloaddition?

作者信息

Jasiński Radomir, Kula Karolina, Kącka Agnieszka, Mirosław Barbara

机构信息

Institute of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Cracow, Poland.

Department of Crystallography, Maria Curie-Skłodowska University, Maria Curie-Skłodowska 3, 20-031 Lublin, Poland.

出版信息

Monatsh Chem. 2017;148(5):909-915. doi: 10.1007/s00706-016-1893-5. Epub 2017 Mar 22.

DOI:10.1007/s00706-016-1893-5
PMID:28458402
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5387018/
Abstract

ABSTRACT

Reactions between ()-2-aryl-1-cyano-1-nitroethenes and diazafluorene lead to acyclic 2,3-diazabuta-1,3-diene derivatives, instead of the expected pyrazoline systems. DFT calculations suggest that this is a consequence of formation of zwitterionic structure in the first stage of the reaction. It must be noted that this is a specific property of the ()-2-aryl-1-cyano-1-nitroethenes group, in contrast to most other conjugated nitroalkenes.

摘要

摘要

（）-2-芳基-1-氰基-1-硝基乙烯与二氮杂芴之间的反应生成的是无环2,3-二氮杂丁-1,3-二烯衍生物，而非预期的吡唑啉体系。密度泛函理论计算表明，这是反应第一阶段形成两性离子结构的结果。必须指出的是，与大多数其他共轭硝基烯烃相比，这是（）-2-芳基-1-氰基-1-硝基乙烯基团的一个特殊性质。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2999/5387018/f3157041c011/706_2016_1893_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2999/5387018/a6aeda962fba/706_2016_1893_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2999/5387018/ad5c85f48197/706_2016_1893_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2999/5387018/f21ea7da5714/706_2016_1893_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2999/5387018/e5cab4f1a88a/706_2016_1893_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2999/5387018/f3157041c011/706_2016_1893_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2999/5387018/a6aeda962fba/706_2016_1893_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2999/5387018/ad5c85f48197/706_2016_1893_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2999/5387018/f21ea7da5714/706_2016_1893_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2999/5387018/e5cab4f1a88a/706_2016_1893_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2999/5387018/f3157041c011/706_2016_1893_Sch3_HTML.jpg

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