First insights into the synthesis of carbo-phospholane and carbo-phospholene oxides

Abstract

Fifteen-membered ring carbo-mers of five-membered rings are considered in the heterocyclic series of the phosphole oxide and less unsaturated parents. The synthesis of the first carbo-phospholane oxides is achieved by a [14+1] two-step/one-pot macrocyclization route with 86 % yield. Reduction of the latter phosphora-[5]pericyclyne with SnCl­2 allowed consistent 1H and 31P NMR characterization of the corresponding carbo-phospholene, produced with 11 % yield. The ultimate carbo-phosphole oxide could not be isolated, but preliminary results on alternative strategies towards this 14 pz-electron Hückel carbo-aromatic are reported.