Intramolecular arene epoxidation by phosphadioxiranes |
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Authors: | Zhang Dong Gao Ruomei Afzal Shabana Vargas Mario Sharma Shantanu McCurdy Alison Yousufuddin Muhammed Stewart Timothy Bau Robert 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: | Singlet oxygen reacts with binaphthyl phosphine derivatives such as 1,1'-binaphthyl di-tert-butyl phosphine to form the corresponding binaphthyl-2-oxide phosphine oxides. This new intramolecular arene epoxidation reaction proceeds with complete retention of stereochemistry. The binaphthyl-2-oxide di-tert-butyl phosphine oxide undergoes a slow "NIH-rearrangement" to form the corresponding hydroxylated product. A transient phosphadioxirane intermediate has been directly observed by low-temperature NMR. Kinetic analyses show that all of the phosphadioxirane intermediate is converted to product. reaction: see text] |
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