Sulfonation of alkenes with sulfur trioxide; reversible stereospecific β-sultone formation
作者:Bert H. Bakker、Hans Cerfontain
DOI:10.1016/s0040-4039(01)80591-8
日期:1989.1
internal and the terminal double bond in the octenes 2a-c and (Z)-1,10-nonadecadiene are evidence for a concerted cycloaddition of sulfur trioxide. The formation of β-sultone 1d is accompanied by 15% of 2-octene-1-sulfonic acid, formed in a primary side-reaction. The sulfonation of the octenes 2a-d to their β-sultones 1a-d is reversible. Desulfonation of the β-sultones 1a-d by water to the olefins 2a-d
在辛烯2a-c和(Z)-1,10-十九碳二烯中,内部和末端双键之间的β-磺内酯形成速率系数的微小差异是三氧化硫协同加成的证据。β-磺酸内酯1d的形成伴随有15%的在初级副反应中形成的2-辛烯-1-磺酸。辛烯2a-d被磺化成它们的β-磺内酯1a-d是可逆的。β-磺内酯1a-d被水脱硫成烯烃2a-d以立体有择的顺式方式进行。