Radomir Jasiński, Karolina Kula, Agnieszka Kącka, Barbara Mirosław
{"title":"(E)-2-芳基-1-氰基-1-硝基乙烯与二氮杂芴的意外反应过程：为什么没有 1,3-二极环化反应？","authors":"Radomir Jasiński, Karolina Kula, Agnieszka Kącka, Barbara Mirosław","doi":"10.1007/s00706-016-1893-5","DOIUrl":null,"url":null,"abstract":"<p><strong>Abstract: </strong>Reactions between (<i>E</i>)-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 (<i>E</i>)-2-aryl-1-cyano-1-nitroethenes group, in contrast to most other conjugated nitroalkenes.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"148 5","pages":"909-915"},"PeriodicalIF":1.7000,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5387018/pdf/","citationCount":"0","resultStr":"{\"title\":\"Unexpected course of reaction between (<i>E</i>)-2-aryl-1-cyano-1-nitroethenes and diazafluorene: why is there no 1,3-dipolar cycloaddition?\",\"authors\":\"Radomir Jasiński, Karolina Kula, Agnieszka Kącka, Barbara Mirosław\",\"doi\":\"10.1007/s00706-016-1893-5\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><strong>Abstract: </strong>Reactions between (<i>E</i>)-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 (<i>E</i>)-2-aryl-1-cyano-1-nitroethenes group, in contrast to most other conjugated nitroalkenes.</p><p><strong>Graphical abstract: </strong></p>\",\"PeriodicalId\":18766,\"journal\":{\"name\":\"Monatshefte Fur Chemie\",\"volume\":\"148 5\",\"pages\":\"909-915\"},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2017-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5387018/pdf/\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Monatshefte Fur Chemie\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1007/s00706-016-1893-5\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2017/3/22 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Monatshefte Fur Chemie","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1007/s00706-016-1893-5","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2017/3/22 0:00:00","PubModel":"Epub","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Unexpected course of reaction between (E)-2-aryl-1-cyano-1-nitroethenes and diazafluorene: why is there no 1,3-dipolar cycloaddition?
Abstract: Reactions between (E)-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 (E)-2-aryl-1-cyano-1-nitroethenes group, in contrast to most other conjugated nitroalkenes.
期刊介绍：
"Monatshefte für Chemie/Chemical Monthly" was originally conceived as an Austrian journal of chemistry. It has evolved into an international journal covering all branches of chemistry. Featuring the most recent advances in research in analytical chemistry, biochemistry, inorganic, medicinal, organic, physical, structural, and theoretical chemistry, Chemical Monthly publishes refereed original papers and a section entitled "Short Communications". Reviews, symposia in print, and issues devoted to special fields will also be considered.
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