Organophosphorus chemistry by David W Allen, David Loakes, John C Tebby (eds.)

By David W Allen, David Loakes, John C Tebby (eds.)

Insurance during this annual assessment of the literature provides a accomplished and demanding survey of the immense box of analysis concerning organophosphorus compounds, from phosphines and phosphonium salts via to phosphorus acids, nucleotides, ylides and phosphazenes. The Editors have additional to the standard content material with a well timed bankruptcy at the fresh advancements in eco-friendly man made ways in organophosphorus chemistry to mirror present pursuits within the quarter

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The formation of zwitterionic phosphonium compounds by nucleophilic attack of phosphorus at unsaturated carbon and the subsequent engagement of such dipolar species in C–C and C–N bond-forming reactions has continued to attract a great deal of attention. Further examples have appeared of the reactions of tertiary phosphines and acetylenic carboxylic acid esters in the presence of a third reactant, commonly a proton source that serves to protonate the initial dipolar species formed to give vinylphosphonium cations.

Also included in this category are reactions leading to carbon–carbon bond formation as typified by the Morita–Bayliss–Hillman (MBH) and related aza-MBH reactions. 183 Among a miscellany of other applications of tertiary phosphines in nucleophilic catalysis are reactions involving the generation of zwitterionic intermediates by addition of phosphines to electrophilic alkenes. 193 As in recent years, phosphinecatalysed additions/cycloadditions to allenoates and related compounds have attracted much attention.

It was found that the stereoselectivity of the procedure is determined during formation of the diastereoisomeric alkoxyphosphonium salts, their initial diastereoisomeric excess limiting the final enantiomeric excess of the phosphines derived therefrom. However, it was also found that a spontaneous Arbuzov decomposition of the intermediate phosphonium salts results in a consistent diastereomeric self-enrichment, with a higher rate constant for decomposition of the minor diastereoisomer. 339 Interest in the chemistry of the 1,3-diphosphacyclobutane-2,4-diradical systems has continued.

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