{"title":"Nitroselenation of carbon-carbon triple bond by PhSeSePh and NO/O2 or NO2","authors":"Yutaka Nishiyama, Mari Sumida, Noboru Sonoda","doi":"10.1002/hc.21480","DOIUrl":null,"url":null,"abstract":"<p>When alkynes were treated with diphenyl diselenide under an atmosphere of nitric oxide and oxygen, nitroselenation of the carbon-carbon triple bond proceeded with a high regioselectivity to give the corresponding 1-nitro-2-phenylseleno alkenes. Similarly, the nitroselenation of alkynes proceeded by the reaction of the alkynes with nitrogen dioxide. The stirring of the 1,2-bis(phenylseleno) alkenes under an atmosphere of nitric oxide and oxygen also gave the corresponding 1-nitro-2-phenylseleno alkenes.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 5-6","pages":""},"PeriodicalIF":1.1000,"publicationDate":"2019-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21480","citationCount":"1","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Heteroatom Chemistry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/hc.21480","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 1
Abstract
When alkynes were treated with diphenyl diselenide under an atmosphere of nitric oxide and oxygen, nitroselenation of the carbon-carbon triple bond proceeded with a high regioselectivity to give the corresponding 1-nitro-2-phenylseleno alkenes. Similarly, the nitroselenation of alkynes proceeded by the reaction of the alkynes with nitrogen dioxide. The stirring of the 1,2-bis(phenylseleno) alkenes under an atmosphere of nitric oxide and oxygen also gave the corresponding 1-nitro-2-phenylseleno alkenes.
期刊介绍:
Heteroatom Chemistry brings together a broad, interdisciplinary group of chemists who work with compounds containing main-group elements of groups 13 through 17 of the Periodic Table, and certain other related elements. The fundamental reactivity under investigation should, in all cases, be concentrated about the heteroatoms. It does not matter whether the compounds being studied are acyclic or cyclic; saturated or unsaturated; monomeric, polymeric or solid state in nature; inorganic, organic, or naturally occurring, so long as the heteroatom is playing an essential role. Computational, experimental, and combined studies are equally welcome.
Subject areas include (but are by no means limited to):
-Reactivity about heteroatoms for accessing new products or synthetic pathways
-Unusual valency main-group element compounds and their properties
-Highly strained (e.g. bridged) main-group element compounds and their properties
-Photochemical or thermal cleavage of heteroatom bonds and the resulting reactivity
-Uncommon and structurally interesting heteroatom-containing species (including those containing multiple bonds and catenation)
-Stereochemistry of compounds due to the presence of heteroatoms
-Neighboring group effects of heteroatoms on the properties of compounds
-Main-group element compounds as analogues of transition metal compounds
-Variations and new results from established and named reactions (including Wittig, Kabachnik–Fields, Pudovik, Arbuzov, Hirao, and Mitsunobu)
-Catalysis and green syntheses enabled by heteroatoms and their chemistry
-Applications of compounds where the heteroatom plays a critical role.
In addition to original research articles on heteroatom chemistry, the journal welcomes focused review articles that examine the state of the art, identify emerging trends, and suggest future directions for developing fields.