The Reaction of 1,2-Naphthoquinones with Some P(III) Derivatives—A Versatile Synthetic Approach to Potentially Useful Naphthoquinones and Dihydroxynaphthalenes Containing Phosphorus–Carbon Bond

Abstract

The reactions of 1,2-naphthoquinones with hexaethyltriaminophosphine or tri(n-butyl)-phosphine followed by bromine or hydrogen bromide treatment has been shown to lead to the quantitative formation of the new 1,2-naphthoquinones and 1,2-dihydroxynaphthalenes containing phosphorus-carbon bond. Its structure established by NMR and single crystal X-ray diffraction.

Keywords:

• 1,2-naphthoquinones
• tri(n-butyl)phosphine
• hexaethyltriamino-phosphire
• 1,2-dihydroxynaphthalenes
• 1,2-naphthoquinone
• one-electron transfer
• betaines
• phosphonium salts
• crystal structure

Acknowledgments

Financial support from RFBR (grant 07-03-00180a) and President of Russian Federation grant (MK-2444.2007.3) is gratefully acknowledged.

Thanks are also expressed to the Mayor of the Kazan City Ilsur R. Metshin and Committee of Youth Affairs of Kazan City Administration for financial support to attend the 17th International Conference on Phosphorus Chemistry (Xiamen, China, 2007).