Intra- and intermolecular reactions of 2-(2,3-epoxypropyl)-1,3,2-benzodioxaphosphole with some five-coordinate phosphorus halides

Citation
Vf. Mironov et al., Intra- and intermolecular reactions of 2-(2,3-epoxypropyl)-1,3,2-benzodioxaphosphole with some five-coordinate phosphorus halides, RUSS J G CH, 69(7), 1999, pp. 1155-1162
Citations number
18
Categorie Soggetti
Chemistry
Journal title
RUSSIAN JOURNAL OF GENERAL CHEMISTRY
ISSN journal
10703632 → ACNP
Volume
69
Issue
7
Year of publication
1999
Pages
1155 - 1162
Database
ISI
SICI code
1070-3632(199907)69:7<1155:IAIRO2>2.0.ZU;2-W
Abstract
Reactions of 2-(2,3-epoxypropyl)-1,3,2-benzodioxaphosphole with bis(o-pheny lenedioxy)chlorophosphorane yield mainly products of beta-cleavage of the o xirane ring, Reactions of 2-(2,3-epoxypropyl)-1,3,2-benzodioxaphosphole wit h dry HCl and HBr result in quantitative formation of stable H-phosphoranes including a 4-halomethyl-1,3,2-dioxaphospholane fragment, Bromination of 2 -(2,3-epoxypropyl)-1,3,2-benzodioxaphosphole with molecular bromine gives 2 ,3-epoxypropyl(o-phenylenedioxy)dibromo as intermediate, in which regiosele ctive intramolecular beta-addition to the oxirane ring affords 2-bromo-4-br omo-methyl-2,2-(o-phenylenedioxy)- 1,3,2-dioxaphospholane. Depending on the reaction conditions, the latter either undergoes cleavage of the dioxaphos pholane ring to form 2-(1,3-dibromo-2-propyl)-1,3,2 lambda(5)-benzodioxapho sphol-2-one or adds to 2-(2,3-epoxypropyl)- 1,3,2-benzodioxaphosphole with formation of bis-phosphoranes or phosphoranyl-containing phosphites.