Ozonolyses of 1,2-Dibenzoylpropene and 1,2-Dibenzoylethylene. Markownikoff's Rule and the Initial Attack of Ozone on an Unsaturated System1
Ozonolyses of 1,2-Dibenzoylpropene and 1,2-Dibenzoylethylene. Markownikoff's Rule and the Initial Attack of Ozone on an Unsaturated System1
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DOI：
10.1021/ja01569a035
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发表时间：
1957-06
影响因子：
15
通讯作者：
P. Bailey;S. S. Bath-S.
中科院分区：
文献类型：
--
作者：
P. Bailey;S. S. Bath-S.
O O O CH，XXIII XXIV O CH，h o XXV XXVI 5.9 µ和2.9 µ处的羟基谱带，并以良好收率还原为1-苯基-1，2-丙二酮（XXIII）。这一反应毫无疑问地表明臭氧攻击的特异性，优先生成苯基乙二醛（XXVI）和两性乙二醛XXV，后者通过与甲醇反应而被捕获，得到XXIV。乍一看，正如在异丁烯和异戊烯的情况下所指出的那样，这些结果似乎是错误的。
O O O CH, XXIII XXIV O CH, h o XXV XXVI5.9 µ and a hydroxyl band at 2.9 µ and reduction to l-phenyl-l, 2-propanedione (XXIII) in good yield. This reaction leaves no doubt concerning the speci-ficity of ozone attack to produce preferentially phenyl glyoxal (XXVI) and zwitterion XXV, which was trapped through its reaction with methanol to give XXIV. At first sight, as pointed out in the cases of iso-butene and camphene, 3 these results seem to be in