CHEMISTRY OF SULFINES, PART V: CHEMOAND STEREOSELECTIVE SYNTHESIS AND HETERO-DIELS-ALDER REACTIONS OF STABLE SULFINES

被引：2
作者：
El Gokha, Ahmed A. [1 ]
Ali, Omar M. [1 ]
Zeid, Ibrahim F. [1 ]
Kudoh, Takayuki [2 ]
El-Sayed, Ibrahim [1 ]
机构：
[1] El Menoufeia Univ, Fac Sci, Dept Chem, Shibin Al Kawm, Egypt
[2] Okayama Univ, Grad Sch Nat Sci & Technol, Dept Med & Bioengn Sci, Tsushima, Okayama, Japan
来源：
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2014年 / 189卷 / 02期
关键词：
Chlorodithioformates; trithiocarbonates; oxidation; sulfines; Diels-Alder; 1,3-dienes; thiopyran S-oxides; X-ray; Ab initio calculations; THIONE S-OXIDES; PUMMERER REARRANGEMENT; SULFUR ADDITION; SINGLET; THERMOCHEMISTRY; NUCLEOPHILES; THIOKETONES; OXIDATION; REAGENT; CARBON;
D O I：
10.1080/10426507.2013.800984
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The stereoselective synthesis of a variety of Z-sulfines by the oxidation of organic trithiocarbonates with m-chloroperbenzoic acid (m-CPBA) is described. Transient E-sulfines that are formed upon heating of Z-sulfines during cycloaddition reactions were trapped with 2,3-dimethyl-1,3-butadiene to yield only one of the possible diastereomers of the functionalized cyclic allylic sulfoxides. An X-ray analysis and ab initio calculations were performed to provide insight into the steric course of the oxidation and cycloaddition reactions. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: Additional tables and figures.]
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页码：185 / 197
页数：13
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