2,2,2-Tribromonaphtho[2,3-d]-1,3,2-Dioxaphosphole: Obtaining and Reaction with Phenylacetylene

Abstract

The reaction of 2,3-dihydroxynaphthalene with phosphorus tribromide followed by bromide treatment has been shown to lead to quantitative formation of the new 2,2,2 tribromonaphtho [2,3-d]-1,3,2-dioxaphosphole. Its interaction with phenylacetylene proceeds by several pathways and leads to unexpected formation of 2-phenyl-9-(2-dihydroxyphosphoryl-1-phenylethen-1-yl)naphtho[1,2-d]furane. The structure of the last compound was established by NMR and single crystal X-ray diffraction.

Keywords:

• 2,3-dihydroxynaphthalenes
• phosphorus tribromides
• phosphole
• phenylacehylene
• naphthofurane
• crystal structure

Acknowledgments

The work is supported by the President of Russian Federation program (MK-2444.2007.3).