The New Data for the Reaction of Arylenedioxy Trihalogenophosphoranes with Alkyl- and Arylacetylenes |
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Authors: | Vladimir F Mironov Alfiya A Shtyrlina Ravil R Petrov Tamara A Baronova Fedor F Alekseev Elena N Varaksina |
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Institution: | A. E. Arbuzov Institute of Organic and Physical Chemistry , Russian Academy of Sciences , Kazan , Russia |
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Abstract: | The new data concerning the reaction between substituted arylenedioxy trihalogenophosphoranes and monoalkyl- or arylacetylenes are summarized. The reaction leads to formation of six-membered heterocycles-2-oxo-4-R-benzo e ]-1,2-oxaphosphorin-3-enes. The substituent effects in the phosphorane and acetylene molecules on the ipso -substitution and halogenation regiochemistry are discussed. The ipso -substitution of tert -butyl group on chlorine and the exchange of bromine on chlorine and iodine on hydrogen have been observed, along with formation of benzophosphorines. The interaction of tetrachloro- ortho -benzoquinone with phosphorus trichloride and arylacetylenes is proposed as a new modification of the reaction leading to the formation of benzo e ]-1,2-oxaphosphorines. The structures of some benzo e ]-1,2-oxaphosphorines are determined by the single crystal X-ray diffraction. |
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Keywords: | Acetylenes Halogenation ipso -substitution Phosphoranes Phosphorus Trichloride Reactions Tetrachloro- ortho -benzoquinone |
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