MECHANISM OF SENSITIZED PHOTOOXYGENATION OF PYRROLES
MECHANISM OF SENSITIZED PHOTOOXYGENATION OF PYRROLES
复制标题
DOI：
10.1021/ja00419a029
复制
发表时间：
1976-01-01
影响因子：
15
通讯作者：
NORRIS, RD
中科院分区：
文献类型：
--
作者：
LIGHTNER, DA;BISACCHI, GS;NORRIS, RD
在染料敏化的烷基吡咯的光氧化反应中，1，4个单线态氧的加入导致了不稳定的内氧化物的形成，低温核磁共振证实了这种内氧化物的存在。已证明内过氧物通过两种机制快速基态反应生成5-羟基-A3-吡咯烷酮：内部重排和与水的反应。通过引入[LSO]水研究了后一种机理的程度，得出的结论是，除在水中外，前一种机理占主导地位。当升温时，N-苯基吡咯内过氧化作用越稳定，就会释放出单线态氧。
In the dye-sensitized photooxygenation of alkylpyrroles, 1, 4 addition of singlet oxygen leads to the formation of un-stable endo-peroxides whose existence was provided by low-temperature NMR. The endo-peroxides havebeen shown to un-dergo rapid ground-state reactions leading, inter alia, to 5-hydroxy-A3-pyrrolinones by two mechanisms: internal rearrange-ment andreaction with water. The extent of the latter mechanism was investigated by the incorporationof [lsO] water with the conclusion that, except in water solvent, the former mechanism predominates. The more stable endo-peroxide of N-phen-ylpyrrole liberates singlet oxygenupon warming.