Reaction of arylenedioxytrihalophosphoranes with acetylenes 12. Alkylacetylenes in the reaction with 2,2,2-trihalobenzo-1,3,2-dioxaphospholes |
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Authors: | A. V. Nemtarev V. F. Mironov E. N. Varaksina A. T. Gubaidullin D. B. Krivolapov R. Z. Musin I. A. Litvinov |
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Affiliation: | 1. A. E. Arbuzov Institute of Organic and Physical Chemistry Kazan Scientific Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation
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Abstract: | A reaction of 2,2,2-trihalobenzo-1,3,2-dioxaphospholes with terminal alkylacetylenes proceeds under mild conditions (~20 °C) and leads to the formation of 4-alkylbenzo[e]-1,2-oxaphosphinine 2-oxide derivatives. The presence of aliphatic substituents in acetylene decreases (as compared to their aromatic counterparts described earlier) regioselectivity of halogenation of benzo fragment in 4-alkylbenzo[e]-1,2-oxaphosphinines: besides predominant 4-alkyl-2,6-dihalobenzo[e]-1,2-oxaphosphinines, minor 2,7- and 2,8-dihalo-substituted 4-alkylbenzo[e]-1,2-oxaphosphinines are formed. An unusual thermal isomerization of 4-alkyl-2-fluorobenzo[e]-1,2-oxaphosphinines to 4-alkylidene-2-fluoro-3,4-dihydrobenzo[e]-1,2-oxaphosphinines was discovered. Molecular and supramolecular structures of some 4-alkylbenzo[e]-1,2-oxaphosphinines were studied by X-ray diffraction analysis. |
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