122703-97-3Relevant articles and documents
OXYPHOSPHORANE ANIONS AS NUCLEOPHILES IN INTRAMOLECULAR DISPLACEMENT REACTIONS
Aksnes, Gunnar
, p. 55 - 62 (2007/10/02)
The present paper reports a kinetic study of alkaline decomposition of four bromoalkyltriphenyl phosphonium bromides with the bromo-substituent in 3-, 4-, 5, and 6-positions, respectively (hereafter designated 3Br-P, 4Br-P, 5Br-P, and 6Br-P), together with the alkaline decomposition of 1,1,4,4-tetrabenzyl-1,4-diphosphoniocyclohexane dibromide (designated 2P).The very high rates of decomposition of 3Br-P and 2P are in accordance with an easy formation of five-membered oxaphospholane ring intermediates through participation of oxyphosphorane anions in intramolecular displacement reactions, with carbon in 3Br-P, and with phosphorus in the neighbouring phosphonium cation of 2P. Key words: Oxyphosphorane anions, bromoalkyltriphenyl phosphonium bromides, 1,1,4,4-tetrabenzyl-1,4-diphosphoniocyclohexane dibromides.