Reaction of (phenylenedioxy)trihalophosphoranes with arylacetylenes: VI. Regiochemistry of the reaction of 2,2,2-trihalo-5-methylbenzo[d][1,3,2]dioxaphospholes with arylacetylenes

NMR and IR spectroscopy and X-ray diffraction were used to show that the reaction of 2,2,2-tri-chloro- and 2,2,2-tribromo-5-methylbenzo[d][1,3,2]dioxaphospholes with para-substituted arylacetylenes proceeds with regioselective formation of 4-aryl-2-halo-7-methyl-2- oxobenzo[e][1,2]oxaphosphorines. W...

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Published inRussian journal of general chemistry Vol. 74; no. 12; pp. 1841 - 1860
Main Authors Mironov, VF, Shtyrlina, AA, Varaksina, EN, Gubaidullin, AT, Azancheev, NM, Dobrynin, AB, Litvinov, AI, Musin, RZ, Konovalov, AI
Format Journal Article
LanguageEnglish
Published NEW YORK MAIK NAUKA/INTERPERIODICA 01.12.2004
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
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Summary:NMR and IR spectroscopy and X-ray diffraction were used to show that the reaction of 2,2,2-tri-chloro- and 2,2,2-tribromo-5-methylbenzo[d][1,3,2]dioxaphospholes with para-substituted arylacetylenes proceeds with regioselective formation of 4-aryl-2-halo-7-methyl-2- oxobenzo[e][1,2]oxaphosphorines. With the trichlorophosphole, selective chlorination of the phenylene fragment in the para position to the endocyclic oxygen atom occurs. With the tribromophosphole, 6-bromo- and unsubstituted benzo[e][1,2]oxaphosphorines are formed as major products. The molecular and supramolecular structure of some of the obtained oxaphosphorines was studied by X-ray diffraction.
ISSN:1070-3632
1608-3350
DOI:10.1007/s11176-005-0108-2