3-Heteraglutaraldehydes. Part III. The 1,2-dithian-4,5-diols and tetra-hydrothiophen-3,4-diols and their oxidation by periodate
作者:Joan E. McCormick、R. S. McElhinney
DOI:10.1039/p19720002795
日期:——
Tris(dimethylamino)phosphine abstracted sulphur from the trans-thiolsulphinate yielding a contracted ring (sulphoxide), whereas tributylphosphine regenerated disulphide by deoxygenation. The dithiandiols reacted readily with Chloramine-T; the trans-compound afforded two isomeric bicyclic sulphenate ester derivatives. Periodate oxidised the tetrahydrothiophendiols to either 3-thia-glutaraldehyde or its 3-oxide
通过改进的方法制备了标题二醇的两种异构体。二噻吩二醇的二乙酸酯容易被氧化成稳定的结晶硫代硫代磺酸盐,而难于硫代硫代磺酸盐。通过硫醇与硫代硫酸盐的反应形成双二硫化物。三(二甲氨基)膦从反式硫代硫酸盐中提取硫,产生缩合环(亚砜),而三丁基膦则通过脱氧再生二硫化物。二硫代二醇容易与氯胺-T反应。该反式-化合物提供了两种异构的双环亚磺酸酯衍生物。高碘酸盐将四氢噻吩二醇氧化为3-硫杂-戊二醛或其3-氧化物,而二硫杂二醇氧化为3,4-二硫杂-己二醛。将氧化速率与其他环状邻位二醇的氧化速率进行了比较。制备了许多衍生物。