By Robert Engel
Synthesis of Carbon-Phosphorus Bonds, moment version is a operating consultant for the laboratory, incorporating classical methods with the new advancements of carbon-phosphorus (C-P) bond formation. those advances comprise the guidance of phosphoranes -- particularly within the use of temporary oxophosphoranes as intermediates in organophosphorus compound synthesis ñ besides the hot methods in the direction of the guidance of compounds with fragrant and vinylic C-P bonds.Synthesis of Carbon-Phosphorus Bonds, moment variation serves as a great tool within the laboratory. It deals special surveys of IUPAC nomenclature thoughts, universal notation platforms, and diverse experimental examples. those positive factors support to make this article a good resource of severe and annotated references, in addition to a a operating consultant for natural and phosphorus chemists particularly, or for any chemists operating with C-P bonds.
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Additional info for Synthesis of carbon-phosphorus bonds
While a “Perkow-route”71–81 for product formation generally ensues when a-halocarbonyl substrates are challenged with Michaelis–Becker reagents,173–175 ethyl 4-bromoacetylacetonate provides a simple substitution product. 146,152,180–182 Although the reaction proceeds using preformed salts of the dialkyl phosphites, 183 the use of tertiary amines facilitates the reaction by allowing all reagent materials to be in solution. 184 Reaction of the dialkyl phosphite in DMF with the appropriate diaryliodonium halide provides the corresponding dialkyl arylphosphonate in good yield (81 to 93%).
Obshch. , 60, 1925, 1990. 34. , A convenient synthesis of primary 2-hydroxyorganophosphines from red phosphorus and oxiranes, Synthesis, 65, 2000. 35. M. , Reactions of elemental phosphorus with organometallic compounds, J. Org. , 29, 471, 1963. fm Page 25 Wednesday, November 19, 2003 10:56 AM 36. M. , Reactions of elemental phosphorus with organometallic compounds and alkyl halides. The direct synthesis of tertiary phosphines and cyclotetraphosphines, J. Org. , 28, 473, 1963. 37. R. , Elemental white phosphorus as a radical trap: a new and general route to phosphonic acids, J.
These proceed in reasonable yield for the preparation of pure organophosphorus materials. fm Page 18 Wednesday, November 19, 2003 10:56 AM hν N S O R. 1. H2 O P4 2. 10 Preparation of phosphonic acids from O-esters of N-hydroxy-z-thiopyridones. 1,1,1,4,4,4-hexafluoro-2-butyne to red phosphorus at elevated temperature. The reaction is catalyzed by elemental iodine, providing the purified product in 45% yield. 11 Formation of a bicyclic from red phosphorus. 12 Direct aryl–C–P bond formation in a bicyclic compound.
Synthesis of carbon-phosphorus bonds by Robert Engel