Addition of diazomethane and sulfur ylides to the carbonyl group in derivatives of ketoses and aldoses-III
作者:Steinar Hagen、Wilber Lwande、Lars Kilaas、Thorleif Anthonsen
DOI:10.1016/0040-4020(80)88039-2
日期:1980.1
The reactions of diazomethane and dimethyloxo-sulfonium methylide with 1,2-dideoxy-4,5-O-isopropylidene-d-glycero-3-pentulose were studied. The sulfur ylide yielded two epimeric epoxides while diazomethane in addition furnished a homologous ketone. The reaction with diazomethane was carried out with varying concentrations of methanol in the reaction medium, and the relative yields of the three products
研究了重氮甲烷和二甲基氧代methyl亚甲基与1,2-二脱氧-4,5 - O-异亚丙基-d-甘油-3-戊糖的反应。内鎓盐生成两种环氧异构体,而重氮甲烷还提供了同源酮。与重氮甲烷的反应是在反应介质中用不同浓度的甲醇进行的,在每种情况下都确定了三种产物的相对产率。在较早提出的两步反应机理的基础上解释了结果。据推测,正氮与一种氧之间的立体效应和络合很重要。