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Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides
Bagi, P.,
Herbay, R.,
Péczka, N.,
Mucsi, Z.,
Timári, I.,
Keglevich, G.:
Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides.
Beilstein J. Org. Chem. 16, 818-832, 2020.
A series of 1-substituted-3-methyl-2-phospholene oxides was prepared from the corresponding 3-phospholene oxides by double bond rearrangement. The 2-phospholene oxides could be obtained by heating the 3-phospholene oxides in methanesulfonic acid, or via the formation of cyclic chlorophosphonium salts. Whereas mixtures of the 2- and 3-phospholene oxides formed, when the isomerization of 3-phospholene oxides was attempted under thermal conditions, or in the presence of a base. The mechanisms of the various double bond migration pathways were elucidated by quantum chemical calculations.
