Reactions of 3,5-di(tert-butyl)-1,2-benzoquinone with terminal acetylenes in the presence of phosphorus trichloride. ipso-Substitution of the tert-butyl group |
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| Authors: | V F Mironov A V Bogdanov A V Nemtarev A A Shtyrlina E N Varaksina V K Cherkasov A B Dobrynin D B Krivolapov R Z Musin I A Litvinov A I Konovalov |
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| Institution: | (1) A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088 Kazan, Russian Federation;(2) G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603950 Nizhny Novgorod, Russian Federation |
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| Abstract: | The reactions of 3,5-di(tert-butyl)-1,2-benzoquinone with aryl-and alkylacetylenes in the presence of phosphorus trichloride afford 4-aryl(alkyl)-8-tert-butyl-2,6-dichloro-2-oxo-2H-benzoe]1,2]oxaphosphinines as the major ipso-substitution products of the tert-butyl group by the chlorine atom. 4-Aryl(alkyl)-6,8-di(tert-butyl)-2,5-dichloro-2-oxo-and 4-aryl(alkyl)-6-tert-butyl-2,8-dichloro-2-oxo-2H-benzoe]1,2]oxaphosphinines were obtained as the minor products. The structures of the stable representatives of this series were
confirmed by X-ray diffraction.
Dedicated to Academician G. A. Abakumov on the occasion of his 70th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1836–1845, September, 2007. |
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| Keywords: | alkynes 1 2-benzoquinones phosphorus trichloride 4 6-di(tert-butyl)-2 2 2-trichlorobenzo-1 3 2-dioxaphosphole ipso-substitution 2H-benzo[e][1 2]oxaphosphinine P-oxides organophosphorus compounds X-ray diffraction study |
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