Reactions of phenylenedioxytrihalophosphoranes with arylacetylenes: 5. Regiochemistry of the reaction of 2,2,2-trichloro-5-chlorocarbonylbenzo[d]-1,3, 2-dioxaphosphole with phenylacetylene. Synthesis and three-dimensional structures of 6-alkylaminocarbonyl-2-oxo-4-phenylbenzo[e]-1,2-oxaphosphorinine derivatives

Article abstract of DOI:10.1023/B:RUCB.0000024850.10750.b9

2,2,2-Trichloro-5-chlorocarbonylbenzo[d]-1,3,2-dioxaphosphole was prepared for the first time by the reaction of protocatechuic acid with phosphorus pentachloride or trichloride followed by chlorination. According to the results of NMR spectroscopy, the reaction of this phosphole with phenylacetylene gave rise to 2,5-dichloro- and 2,8-dichloro-6-chlorocarbonyl-2-oxo-4-phenylbenzo[e]- 1,2-oxaphosphorinines as the major products. The molecular and supramolecular structures of their stable derivatives, viz., 2-tert-butylamino-6-tert- butylaminocarbonyl-5-chloro-2-oxo-4-phenylbenzo[e]-1,2-oxaphosphorinine and isopropylammonium 8-chloro-6-isopropylaminocarbonyl-2-oxo-4-phenylbenzo[e]-1,2- oxaphosphorinin-2-oate, respectively, were established by X-ray diffraction analysis.