Dawid T. Leja, Wojciech J. Depa, Piotr A. Guńka, J. Zachara, Jaromir B. Lechowicz, G. Groszek
{"title":"源自二硫代乙醛的新型杂环有机硫化合物","authors":"Dawid T. Leja, Wojciech J. Depa, Piotr A. Guńka, J. Zachara, Jaromir B. Lechowicz, G. Groszek","doi":"10.1055/a-2259-3689","DOIUrl":null,"url":null,"abstract":"The dithioacetalization of lactaldehyde derivatives with ethane-1,2-, propane-1,3-; butane-1,4- and pentane-1,5-dithiols in the presence of 4 mol% of scandium triflate has been described. A series of cyclic dithioacetals were obtained with yields ranging from quantitative to 37%. The dithioacetalization of lactaldehyde derivatives with butane-1,4-dithiol and pentane-1,5-dithiol groups are accompanied by the formation of 14- and 16-membered macrocyclic sulfur structures with yields of 3% and 18%, respectively. In the case of a cyclic dithioacetal derivative with three methylene groups, a diastereoisomeric pair of enantiomers was obtained, the structure of which was confirmed by single-crystal X-ray diffraction analysis. Dithioacetals are useful building blocks in the synthesis of complex chemical structures, macrocyclic compounds can be used to complex metal ions.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"18 3","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"New heterocyclic organosulfur compounds derived from dithioacetals\",\"authors\":\"Dawid T. Leja, Wojciech J. Depa, Piotr A. Guńka, J. Zachara, Jaromir B. Lechowicz, G. Groszek\",\"doi\":\"10.1055/a-2259-3689\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The dithioacetalization of lactaldehyde derivatives with ethane-1,2-, propane-1,3-; butane-1,4- and pentane-1,5-dithiols in the presence of 4 mol% of scandium triflate has been described. A series of cyclic dithioacetals were obtained with yields ranging from quantitative to 37%. The dithioacetalization of lactaldehyde derivatives with butane-1,4-dithiol and pentane-1,5-dithiol groups are accompanied by the formation of 14- and 16-membered macrocyclic sulfur structures with yields of 3% and 18%, respectively. In the case of a cyclic dithioacetal derivative with three methylene groups, a diastereoisomeric pair of enantiomers was obtained, the structure of which was confirmed by single-crystal X-ray diffraction analysis. Dithioacetals are useful building blocks in the synthesis of complex chemical structures, macrocyclic compounds can be used to complex metal ions.\",\"PeriodicalId\":509029,\"journal\":{\"name\":\"Synlett\",\"volume\":\"18 3\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-02-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synlett\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1055/a-2259-3689\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synlett","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2259-3689","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
New heterocyclic organosulfur compounds derived from dithioacetals
The dithioacetalization of lactaldehyde derivatives with ethane-1,2-, propane-1,3-; butane-1,4- and pentane-1,5-dithiols in the presence of 4 mol% of scandium triflate has been described. A series of cyclic dithioacetals were obtained with yields ranging from quantitative to 37%. The dithioacetalization of lactaldehyde derivatives with butane-1,4-dithiol and pentane-1,5-dithiol groups are accompanied by the formation of 14- and 16-membered macrocyclic sulfur structures with yields of 3% and 18%, respectively. In the case of a cyclic dithioacetal derivative with three methylene groups, a diastereoisomeric pair of enantiomers was obtained, the structure of which was confirmed by single-crystal X-ray diffraction analysis. Dithioacetals are useful building blocks in the synthesis of complex chemical structures, macrocyclic compounds can be used to complex metal ions.