PSEUDOROTATION IN MONOCYCLIC OXYPHOSPHORANES WHICH CONTAIN CHIRAL CENTERS |
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Authors: | Donald B Denney Dorothy Z Denney Micah N Raab |
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Institution: | Department of Chemistry, Rutgers , The State University of New Jersey , New Brunswick, N.J., 08853 |
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Abstract: | Abstract Phenylbis2-methyl-1-butoxy]phosphine has been allowed to react with butanedione to produce 2,2-bis2-methyl-1-butoxy]-2-phenyl-4,5-dimethyl-1,3,2-dioxaphophol-4-ene. This material is a mixture of three diastereomers. It has been reported that 2,2-bistetrahydrofurfuyloxy]-2-phenyl-4,5-dimethyl-1,3,2-dioxaphosphol-4-ene is a mixture of only two diastereomers. The present work suggest that two of the diastereomers of the tetrahydrofurfuryloxy compound interconvert via hexacoordinated zwitterionic intermediates which involve addition of the oxygen of the tetrahydrofuran ring to phosphorus. |
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Keywords: | Pseudorotation monocyclic phosphoranes strain rule hexacoordinate phosphorus |
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