ORGN 100 |
| Primary phosphines are valuable compounds with a wide range of potential applications. In particular, we sought to use them as precursors to chiral phosphorus ligands with a range of functionality. However, they have a reputation as being spontaneously flammable, toxic, highly air-sensitive materials and as such they are an under-utilised class of compound. In contrast to this, we have prepared MOP-type chiral primary phosphines that demonstrate a remarkable degree of air-stability. The resistance to air oxidation of phosphine (I) allowed an X-ray crystal structure to be obtained, the first of its kind. Such stability is rare; we present here the results of our structure-reactivity investigation that suggest this is attributable to neither sterics nor negative hyperconjugation, both proposed as stabilising factors for certain achiral cases. Our findings signify that these compounds are ideal precursors to novel asymmetric phosphine ligands.
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Asymmetric Reactions and Syntheses, Physical Organic Chemistry, Combinatorial Chemistry, Total Synthesis
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Organic Chemistry |
