Deng-Ke Cao, Yuelie. Lu, T. Zheng
Feb 25, 2013
Citations
0
Influential Citations
5
Citations
Journal
RSC Advances
Abstract
Reaction of the cyclic phosphonate ester of anthracen-9-yl(5,5-dimethyl-2-oxo-2λ5-1,3,2-dioxaphosphinan-2-yl)-methanol (1) with TMSBr unexpectedly generated phosphonates 2-(10-bromoanthracen-9-ylmethyl)-5,5-dimethyl-2λ5-1,3,2-dioxa-phosphinan-2-one (2) and (10-bromoanthrancen-9-yl)methyl-phosphonate mono(3-bromo-2,2′-dimethylpropyl) ester (3) through a series of bond cleavages and formations. Compound 3 could transform into 2 in CH3OH–H2O solution, but it is stable in dry CH3CN. The structures of 1–3 have been characterized by IR spectra, 1H NMR spectra, and crystal structures. In contrast to 1, the dioxaphosphorinane ring is open in 3, but not changed in 2. In addition, both 2 and 3 contain a bromine-substituted anthracene group, and have no hydroxyl group as that in 1. For compounds 1–3, their crystal structures and fluorescent properties in CH2Cl2 solution and in the solid state have been studied.