199387-45-6Relevant articles and documents
Remarkable dependence of the regioselectivity of free radical additions to 3-cinnamoyloxazolidin-2-ones on the stability of the intermediate adduct-radical, electrophilicity of the adding radicals and the conditions for their generation
Tararov, Vitali I.,Kuznetzov, Nikolai Yu.,Bakhmutov, Vladimir I.,Ikonnikov, Nikolai S.,Bubnov, Yuri N.,Khrustalev, Victor N.,Saveleva, Tatiana F.,Belokon, Yuri N.
, p. 3101 - 3106 (1997)
Electrophilic (CCl3) and nucleophilic radicals (Pri) are found to add at 80°C to the C=C bond of 3-(E)-cinnamoyl-4-phenyloxazolidin-2-one 1a and 3-(E)-cinnamoyl-4-benzyloxazolidin-2-one 1b predominantly at the α-position of the bond. While for the CCl3 radical no product of β-addition has been found, for the Pri radical such a path constitutes up to 40% of the whole process at 80°C. An interplay between the stability of the intermediate adduct radicals and the electrophilicity or nucleophilicity of the radicals undergoing addition are invoked to rationalize the observation. At a low temperature (-23°C) β-addition of the Pri radical becomes the dominant process (up to 75%).
