K. N. Sedenkova, D. V. Savchenkova, O. V. Ryzhikova, Yu. K. Grishin, E. B. Averina
{"title":"叠氮化钠处理 1,6,10,14-四氧杂螺[2.1.25.1.29.1.213.13]十六烷时的立体依赖性亲核开环反应","authors":"K. N. Sedenkova, D. V. Savchenkova, O. V. Ryzhikova, Yu. K. Grishin, E. B. Averina","doi":"10.1007/s11172-024-4330-7","DOIUrl":null,"url":null,"abstract":"<div><p>Nucleophilic ring-opening of 1,6,10,14-tetraoxatetraspiro[2.1.2<sup>5</sup>.1.2<sup>9</sup>.1.2<sup>13</sup>.1<sup>3</sup>]hexadecane, a cyclooctane structure spiro-fused with four oxirane fragments, under the action of sodium azide was studied. Depending on the relative configuration of stereocenters in the starting compound, the reaction proceeded as an intramolecular transannular cyclization with the formation of a 9-oxabicyclo[3.3.1]nonane skeleton or as an independent nucleophilic opening of the oxirane rings, leading to tetraazido tetraols of the cyclooctane series.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 7","pages":"2105 - 2109"},"PeriodicalIF":1.7000,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Stereo-dependent nucleophilic ring-opening of 1,6,10,14-tetraoxatetraspiro[2.1.25.1.29.1.213.13]hexadecane upon treatment with sodium azide\",\"authors\":\"K. N. Sedenkova, D. V. Savchenkova, O. V. Ryzhikova, Yu. K. Grishin, E. B. Averina\",\"doi\":\"10.1007/s11172-024-4330-7\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Nucleophilic ring-opening of 1,6,10,14-tetraoxatetraspiro[2.1.2<sup>5</sup>.1.2<sup>9</sup>.1.2<sup>13</sup>.1<sup>3</sup>]hexadecane, a cyclooctane structure spiro-fused with four oxirane fragments, under the action of sodium azide was studied. Depending on the relative configuration of stereocenters in the starting compound, the reaction proceeded as an intramolecular transannular cyclization with the formation of a 9-oxabicyclo[3.3.1]nonane skeleton or as an independent nucleophilic opening of the oxirane rings, leading to tetraazido tetraols of the cyclooctane series.</p></div>\",\"PeriodicalId\":756,\"journal\":{\"name\":\"Russian Chemical Bulletin\",\"volume\":\"73 7\",\"pages\":\"2105 - 2109\"},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2024-08-31\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Russian Chemical Bulletin\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s11172-024-4330-7\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Chemical Bulletin","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11172-024-4330-7","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Stereo-dependent nucleophilic ring-opening of 1,6,10,14-tetraoxatetraspiro[2.1.25.1.29.1.213.13]hexadecane upon treatment with sodium azide
Nucleophilic ring-opening of 1,6,10,14-tetraoxatetraspiro[2.1.25.1.29.1.213.13]hexadecane, a cyclooctane structure spiro-fused with four oxirane fragments, under the action of sodium azide was studied. Depending on the relative configuration of stereocenters in the starting compound, the reaction proceeded as an intramolecular transannular cyclization with the formation of a 9-oxabicyclo[3.3.1]nonane skeleton or as an independent nucleophilic opening of the oxirane rings, leading to tetraazido tetraols of the cyclooctane series.
期刊介绍：
Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections:
General and Inorganic Chemistry;
Physical Chemistry;
Organic Chemistry;
Organometallic Chemistry;
Chemistry of Natural Compounds and Bioorganic Chemistry.
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