Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

• Péter Bagi,
• Réka Herbay,
• Nikolett Péczka,
• Zoltán Mucsi,
• István Timári and
• György Keglevich

Beilstein J. Org. Chem. 2020, 16, 818–832, doi:10.3762/bjoc.16.75

• -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. Keywords: chlorophosphonium salts; isomerization; 2-phospholene oxides; 3-phospholene oxides; quantum chemistry; Introduction P-Heterocyclic derivatives are valuable targets in synthetic organophosphorus chemistry [1][2][3

• thermal conditions, in the presence of acids or bases or via the formation of chlorophosphonium salts. In our study, the 3-methyl-3-phospholene oxides were considered as model compounds, the double bond rearrangement of a 3-phospholene oxide and a 3,4-dimethyl-3-phospholene oxide was also investigated