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Synthesis, structure and reactivity of some chiral benzylthio alcohols, 1,3-oxathiolanes and their S-oxides
Journal of Sulfur Chemistry ( IF 2.2 ) Pub Date : 2020-04-24 , DOI: 10.1080/17415993.2020.1754418
R. Alan Aitken 1 , Philip Lightfoot 1 , Andrew W. Thomas 1
Affiliation  

ABSTRACT A series of amino acid-derived chiral benzylthio alcohols have been prepared and characterized. A chiral mercapto alcohol derived from S-leucine has been used to form three chiral 2,4-disubstituted 1,3-oxathiolanes. One of these has been oxidized to the S-oxide and another to the S,S-dioxide. The cis and trans isomers have been characterized by 1H NMR in each case and it appears that thermal epimerisation at C-2 is possible at the sulfoxide oxidation state. The X-ray structure of major trans diastereomer of 2-phenyl-4-isobutyl-1,3-oxathiolane S,S-dioxide shows an envelope conformation with oxygen at the flap and an internal angle at sulfur of just 93.8°. This compound fragments upon flash vacuum pyrolysis at 700°C to give SO2, benzaldehyde and 4-methylpent-1-ene. GRAPHICAL ABSTRACT

中文翻译:

一些手性苄硫醇、1,3-氧杂硫杂环戊烷及其硫氧化物的合成、结构和反应性

摘要 已经制备并表征了一系列氨基酸衍生的手性苄硫醇。衍生自 S-亮氨酸的手性巯基醇已被用于形成三个手性 2,4-二取代 1,3-氧杂硫杂环戊烷。其中一个已被氧化为 S-氧化物,另一个已被氧化为 S,S-二氧化物。在每种情况下,顺式和反式异构体均已通过 1 H NMR 表征,并且似乎在亚砜氧化态下 C-2 处的热差向异构化是可能的。2-苯基-4-异丁基-1,3-氧杂硫杂环戊烷 S,S-二氧化物的主要反式非对映体的 X 射线结构显示了一个包膜构象,在襟翼处有氧,在硫处的内角仅为 93.8°。该化合物在 700°C 下进行快速真空热解时会碎裂,生成 SO2、苯甲醛和 4-甲基戊-1-烯。图形概要
更新日期:2020-04-24
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