Oxymetallation. Part IV. The reaction of derivatives from the t-butyl-peroxymercuration of αβ-unsaturated esters and ketones with sodium borohydride
作者:A. J. Bloodworth、R. J. Bunce
DOI:10.1039/p19720002787
日期:——
by t-butylperoxy-mercuration of isopropenyl methyl ketone (Y = Me) and methyl methacrylate (Y = OMe), affords the previously unknown α-carbonyl-substituted peroxides Me2C(OOBut)COY mixed with 10 and 30 mole % respectively of the corresponding epoxides. Similar treatment of the compounds R1R2C(OOBut)CH(HgOAc)CO2Me, obtained from four αβ-unsaturated esters, gives cleanly and in high yield the β-meth
硼氢化钠还原由异丙烯基甲基酮(Y = Me)和甲基丙烯酸甲酯(Y = OMe)的叔丁基过氧化汞缩合形成的化合物XHgCH 2 CMe(OOBu t)COY Me 2 C(OOBu t)COY过氧化物分别与10和30摩尔%的相应环氧化物混合。由四种αβ-不饱和酯制得的化合物R 1 R 2 C(OOBu t)CH(HgOAc)CO 2 Me的相似处理可干净而高收率地产生β-甲氧基羰基过氧化物R 1 R 2 C(OOBu t)-CH 2 CO 2Me,代表这种类型化合物的一般化且大大改善的合成方法。相反,来自查尔酮的相关过氧汞(PhCH CHBz)产生了高产率的查尔酮氧化物,而来自均三甲苯醚的过氧化汞主要提供了二烷基汞,[Me 2 C(OOBu t)CH(COMe)] 2 Hg。在这些条件下,对称地对称来自查尔酮和氧化异丁烯的R 1 R 2 C(OMe)CH(HgOAc)COR的甲氧基汞。