Regioselectivity observed in manganese(III) acetate mediated addition of acetylacetone to various alkenes: mechanistic and theoretical studies
作者:Selin Ceyhan、Yasin Cetinkaya、Akin Akdag、Metin Balci
DOI:10.1016/j.tet.2016.09.015
日期:2016.10
were formed. Stilbene derivatives also gave two regioisomers under the same reaction conditions. However, 1-methoxy-4-(4-nitrostyryl)benzene provided a single cycloaddition product. The observed regioselectivity was discussed in terms of atomic charge distribution on the olefinic double bond carbon atoms. Furthermore, activation barriers for transition states were calculated.
在乙酸中Mn(OAc)3的存在下,用乙酰丙酮处理1,2-位被2-硫代苯基,3-硫代苯基和被吸电子基团和供电子基团取代的苯基的各种烯烃。在噻吩环在C-2碳原子连接至双键的情况下,形成单个区域异构体,而在C-3位置取代的情况下,形成两个区域异构体。在相同的反应条件下,二苯乙烯衍生物也产生了两种区域异构体。然而,1-甲氧基-4-(4-硝基苯乙烯基)苯提供了单一的环加成产物。根据在烯烃双键碳原子上的原子电荷分布,讨论了观察到的区域选择性。此外,计算了过渡态的激活势垒。