Reactions of phenylenedioxytrihalophosphoranes with arylacetylenes: XIII. Reaction of 5-tert-butyl-2,2,2-trihalo-1,3,2λ5-benzodioxaphospholes with acetylenes

Reactions of 5- tert -butyl-2,2,2-trichloro-, 2,2,2-tribromo-5- tert -butyl-, and 2,2-dibromo-5- tert -butyl-2-fluoro-1,3,2λ 5 -benzodioxaphospholes with aryl- and alkylacetylenes lead to quantitative formation of 2-halo-1,2λ 5 -benzoxaphosphinine 2-oxides which may be regarded as phosphorus analogs...

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Published in:Russian journal of organic chemistry 2014-06, Vol.50 (6), p.864-887
Main Authors: Mironov, V. F., Nemtarev, A. V., Varaksina, E. N., Shtyrlina, A. A., Gubaidullin, A. T., Litvinov, I. A., Dobrynin, A. B.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:Reactions of 5- tert -butyl-2,2,2-trichloro-, 2,2,2-tribromo-5- tert -butyl-, and 2,2-dibromo-5- tert -butyl-2-fluoro-1,3,2λ 5 -benzodioxaphospholes with aryl- and alkylacetylenes lead to quantitative formation of 2-halo-1,2λ 5 -benzoxaphosphinine 2-oxides which may be regarded as phosphorus analogs of natural heterocyclic compounds, coumarin and chromene. The major products (>70%) are 4-aryl-7- tert -butyl-2,6-dichloro-, 4-aryl-2-bromo-7- tert -butyl-, and 4-aryl-7- tert -butyl-2-fluoro-1,2λ 5 -benzoxaphosphinine 2-oxides. Hydrolysis of these compounds and their treatment with amines gives the corresponding 2-hydroxy and 2-amino derivatives, as well as ammonium salts. The structure of some compounds was proved by X-ray analysis.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428014060190