Sereoselective Addition of Benzaldehyde N,N-Dimethyl-Hydrazone to 2-RfO-4-Oxo-5,6-Benzo-1,3,2-Dioxaphosphorinanes. The Spatial Structure of 2-Pentafluorophenoxy-4-Dimethylamino-2,5-Dioxo-3-Phenyl-6,7-Benzo-1,4,2-Oxazaphosphepine |
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| Authors: | Vladimir F. Mironov Aidar T. Gubaidullin Gulnara A. Ivkova Igor A. Litvinov Boris I. Buzykin Liliya M. Burnaeva |
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| Affiliation: | 1. Organic and Physical Chemistry A.E. Arbuzov Institute , Kazan , 420088 , Russia;2. Kazan State University , Kazan , 420008 , Russia |
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| Abstract: | Abstract [3+2]-Cycloaddition of N,N-dimethylhydrazone benzaldehyde (I) to 2-RFO-4-oxo-5,6-benzo-l,3,2-dioxaphosphorinanes (II) yields the new heterocycle - 2-RFO-4-Me2N-2,5-dioxo-3-phenyl-6,7-benzo- 1,4,2-dioxaphosphepine (III) [RF = C6F5, CH(CF3)2) with high stereoselectivity (above 94%). The reaction is likely to involve the initial interaction of nitrogen as a nucleophile with wbonyl carbon as an electrophile. The hydrolysis of (III) leads to phosphonic acid (IV) (ORF = OH). |
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