The chemistry of 1-acylphosphirane complexes: A phosphorus analogue of the Cloke-Wilson rearrangement

The stabilization of the phosphirane ring by complexation to tungsten pentacarbonyl allows the emergence of the Cloke-Wilson rearrangement in the 1-acylphosphirane complexes around 130oC. Contrary to the cyclopropane case, this transformation of the 1-acylphosphirane to the 1,3-oxaphosphol-3-ene complexes is reversible. It is favored by a 2-phenyl and, even more, a 2-vinyl substitution. The 1,3-oxaphosphol-3-ene complexes are trapped by conjugated dienes.