K. M. H. Hilmy, I. El-Sayed, S. El-kousy, H. S. Slem
{"title":"C-Sulfonyldithioformates as heterodienophiles and enophiles in [4 + 2] cycloaddition and ene reactions","authors":"K. M. H. Hilmy, I. El-Sayed, S. El-kousy, H. S. Slem","doi":"10.1080/02786110310001619978","DOIUrl":null,"url":null,"abstract":"C-Sulfonyldithioformates 3 have been shown to be super-heterodienophiles in [4 + 2] cycloadditions with acyclic and cyclic dienes. Acyclic 1,3-dienes react with 3 in chloroform at room temperature to give the corresponding dihydrothiopyrans 4–6, while cyclopentadiene reacts with 3 to afford endo- and exo-2-thiabicyclo[2.2.1]heptene 7. Furthermore, the enophilic properties of 3 have been demonstrated by reacting 3 with tetramethylallene, 1-butene and trans-2-butene to afford the corresponding ene adducts 9, 10 and 11 respectively in quantitative yields.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":"36 1","pages":"187 - 193"},"PeriodicalIF":0.0000,"publicationDate":"2003-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Sulfur Letters","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1080/02786110310001619978","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 1
Abstract
C-Sulfonyldithioformates 3 have been shown to be super-heterodienophiles in [4 + 2] cycloadditions with acyclic and cyclic dienes. Acyclic 1,3-dienes react with 3 in chloroform at room temperature to give the corresponding dihydrothiopyrans 4–6, while cyclopentadiene reacts with 3 to afford endo- and exo-2-thiabicyclo[2.2.1]heptene 7. Furthermore, the enophilic properties of 3 have been demonstrated by reacting 3 with tetramethylallene, 1-butene and trans-2-butene to afford the corresponding ene adducts 9, 10 and 11 respectively in quantitative yields.
c -磺酰基二硫甲酸酯3在[4 + 2]与无环和环二烯的环加成中被证明是超杂二烯亲和物。无环1,3-二烯在室温下与3在氯仿中反应得到相应的二氢噻吩4-6,环戊二烯与3反应得到内、外2-噻吩环[2.2.1]庚烯7。此外,通过与四甲基亚烯、1-丁烯和反式-2-丁烯反应,3的亲和性得到了相应的烯加合物9、10和11的定量产率。