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Synthesis of Phosphane Oxides and Phosphonates by Cerium‐Mediated Addition of Organolithium Compounds to Chloro‐Phosphorus Compounds
Author(s) -
Dalpozzo Renato,
De Nino Antonio,
Miele Daniela,
Tagarelli Antonio,
Bartoli Giuseppe
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199909)1999:9<2299::aid-ejoc2299>3.0.co;2-y
Subject(s) - chemistry , moiety , reagent , halide , phosphorus , cerium , yield (engineering) , organic chemistry , chloride , medicinal chemistry , inorganic chemistry , metallurgy , materials science
The addition of organocerium reagents 2a–g to phosphinoyl chloride 1a or chlorophosphates 1b leads to the synthesis of phosphane oxides 3aa–ag and phosphonates 3bb , be in good to high yield. The reaction can be extended to cerium enolates 4 (of ketones) and 6 (of nitriles) except when a benzyl group bound to the carbonyl moiety should be metallated. The latter reaction is the first reported synthesis of β‐oxophosphane oxides by a simple reaction between enolates and a phosphorus(V) halide.