53369-64-5Relevant academic research and scientific papers
Photochemistry of Uracils in Halogenated Solvents
Moltke-Leth, Claus,Joergensen, Karl Anker
, p. 1487 - 1490 (2007/10/02)
The photochemistry of uracil and 1-substituted and 1,3-disubstituted uracils in CHBr3-CH2Cl2 is investigated.Photolysis of uracil leads to the formation of 5,6-dibromo-5,6-dihydrouracil as the main product, with 5-bromouracil as the by-product.In contrast with this the 5-bromouracils are formed as the main products by the photolysis of 1-substituted and 1,3-disubstituted uracils, with the corresponding 5,6-dihydro- and 5-bromo-5,6-dihydrouracils as the by-products.The kinetics of the bromination reaction have also been investigated and based on these results a free radical mechanism is proposed.
Selective Oxidative Halogenation of Uracils
Moltke-Leth, Claus,Joergensen, Karl Anker
, p. 1117 - 1121 (2007/10/02)
A variety of N-substituted uracils has been selectively brominated to the corresponding 5-bromouracils in high yield by CHBr3-O2.Both oxidative bromination and chlorination of N-substituted uracils can be performed by means of combination of haloalkane solvents with m-chloroperbenzoic acid, magnesium monoperoxyphthalate, tert-butyl hydroperoxide or iodosylbenzene.Intermediates along the reaction path leading to the 5-halouracils have been identified; the intermediates depend on the oxidant used.Mechanistic aspects of the halogenation reactions and the reactive intermediates are discussed.
