Phosphadioxirane: a peroxide from an ortho-substituted arylphosphine and singlet dioxygen |
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Authors: | Ho David G Gao Ruomei Celaje Jeff Chung Ha-Yong Selke Matthias |
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Institution: | Department of Chemistry and Biochemistry, California State University, Los Angeles, Los Angeles, CA 90032, USA. |
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Abstract: | We prepared the primary adduct for the reaction of singlet dioxygen (1O2) with an arylphosphine by using the sterically hindered arylphosphine tris(o-methoxyphenyl)phosphine. The resulting phosphadioxirane has a dioxygen molecule triangularly bound to the phosphorus atom. Olefin trapping experiments show that the phosphadioxirane can undergo nonradical oxygen atom-transfer reactions. Under protic conditions, two different intermediates are formed during the reaction of singlet dioxygen with tris(o-methoxyphenyl)phosphine, namely, the corresponding hydroperoxy arylphosphine and a hydroxy phosphorane. Experiments with other arylphosphines possessing different electronic and steric properties demonstrate that the relative stability of the tris(o-methoxyphenyl)phosphadioxirane is due to both steric and electronic effects. |
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