Reaction of trihalo(phenylenedioxy)phosphoranes with acetylenes: X. specific features of the reactions of substituted 2,2,2-trichloro-1,3,2λ5-benzodioxaphospholes with 3-chloro(bromo, iodo)propynes |
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Authors: | V F Mironov E N Varaksina A A Shtyrlina A T Gubaidullin N M Azancheev R S Musin I A Litvinov A I Konovalov |
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Institution: | (1) Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, Tatarstan, 420088, Russia |
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Abstract: | It was shown for the first time that 3-chloro-, 3-bromo-, and 3-iodopropynes can react with 2,2,2-trichloro-, 2,2,2-trichloro-5-methyl-, and 5,6-dibromo-2,2,2-trichloro-1,3,2λ5-benzodioxaphospholes to give derivatives of 4-(halomethyl)-2-chloro-2H-1,2λ5-benzoxaphosphinin-2-ones. The reaction involves nonselective chlorination of the phenylene substituent in different positions, and the resulting isomer ratio is temperature-dependent. In the reactions of 3-bromo-and 3-iodopropynes with 2,2,2-trichloro-1,3,2λ5-benzo-dioxaphosphole, a side process takes place, viz. nucleophilic substitution of bromine and iodine with chlorine. The structure of some of the prepared 4-(chloromethyl)-1,2-benzoxaphosphinines was studied by means of X-ray diffraction. |
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