Issue 3, 2009

The chemistry of phosphorodiselenoates: structure, catalysis and formation of Se-esters

Abstract

Though metal complexes of dialkyl diselenophosphate ligands [Se2P(OR)2] (dsep) have been reported in several occasions, the solid-state structure of isolated dsep ligands is still unknown. Herein the ammonium salt of the dsep ligand, NH4Se2P(OiPr)2, is structurally characterized and N–H⋯Se type of H-bonding interactions are revealed. In addition, the NH4Se2P(OR)2 ligands serve as an ammonia source in the Fe powder catalyzed condensation of acetone with ammonia to form 2,2,6,6-tetramethyl-4-oxopiperidinium salts of the dsep ligand, [{H2N(CH2)2(CMe2)2CO}{Se2P(OR)2}] (1a = iPr, 1b = Et) of which 1b is structurally characterized. Novel syntheses of Se-esters of O,O′-dialkylphosporodiselenoic acid, 2, 3, 4, 5, 6, 7, directly from the ammonium salts have been achieved. The reactions, where one of the Se atoms of the dsep unit acts as the nucleophilic center, include Michael addition, epoxide ring opening addition, acylation and α-alkynation.

Graphical abstract: The chemistry of phosphorodiselenoates: structure, catalysis and formation of Se-esters

Supplementary files

Article information

Article type
Paper
Submitted
31 Jul 2008
Accepted
27 Oct 2008
First published
11 Dec 2008

New J. Chem., 2009,33, 626-633

The chemistry of phosphorodiselenoates: structure, catalysis and formation of Se-esters

B. Sarkar, C. Fang, L. You, J. Wang and C. W. Liu, New J. Chem., 2009, 33, 626 DOI: 10.1039/B813267D

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