Synthesis of polytertiary phosphines and 'mixed' phosphorus-sulphur and 'mixed' phosphorus-nitrogen polydentate ligands via free-radical catalysis

Daniel L DuBois, William H. Myers, Devon W. Meek

Research output: Contribution to journalArticle

71 Citations (Scopus)

Abstract

In the presence of free radicals, phosphorus-hydrogen and sulphur-hydrogen bonds cleanly and readily add to the carbon-carbon double bonds of vinyl derivatives to produce organic compounds that are useful as polydentate chelating ligands. The generality and mild conditions of the reaction are demonstrated by the synthesis of di-, tri-, and tetra-(tertiary phosphines) and of compounds that contain both phosphorus and sulphur or phosphorus and nitrogen donor groups. This free-radical-catalysed addition of molecules containing P-H and S-H bonds to vinyl compounds provides a general valuable alternative to the base-catalysed addition method.

Original languageEnglish
Pages (from-to)1011-1015
Number of pages5
JournalJournal of the Chemical Society, Dalton Transactions
Issue number11
DOIs
Publication statusPublished - 1975

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Phosphines
Sulfur
Phosphorus
Catalysis
Free Radicals
Nitrogen
Ligands
Vinyl Compounds
Carbon
Chelation
Organic compounds
Hydrogen
Hydrogen bonds
Derivatives
Molecules

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "In the presence of free radicals, phosphorus-hydrogen and sulphur-hydrogen bonds cleanly and readily add to the carbon-carbon double bonds of vinyl derivatives to produce organic compounds that are useful as polydentate chelating ligands. The generality and mild conditions of the reaction are demonstrated by the synthesis of di-, tri-, and tetra-(tertiary phosphines) and of compounds that contain both phosphorus and sulphur or phosphorus and nitrogen donor groups. This free-radical-catalysed addition of molecules containing P-H and S-H bonds to vinyl compounds provides a general valuable alternative to the base-catalysed addition method.",
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AU - Myers, William H.

AU - Meek, Devon W.

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AB - In the presence of free radicals, phosphorus-hydrogen and sulphur-hydrogen bonds cleanly and readily add to the carbon-carbon double bonds of vinyl derivatives to produce organic compounds that are useful as polydentate chelating ligands. The generality and mild conditions of the reaction are demonstrated by the synthesis of di-, tri-, and tetra-(tertiary phosphines) and of compounds that contain both phosphorus and sulphur or phosphorus and nitrogen donor groups. This free-radical-catalysed addition of molecules containing P-H and S-H bonds to vinyl compounds provides a general valuable alternative to the base-catalysed addition method.

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