SYNTHESIS AND CHARACTERIZATION OF 6-SUBSTITUTED DIBENZO [d,f] [1,3,2] DIOXA PHOSPHEPIN 6-OXIDES

Abstract

Several 6-trichloromethyl dibenzo[di] [1.3.2] dioxaphosphepin 6-oxide (3a), 2-chloroethoxy dibenzo[di] [1.3.2] dioxaphosphepin 6-oxide (3b) and alkylcarbamato dibenzo [di] [1.3.2] dioxaphosphepin 6-oxides (6a-c) have been synthesized from reactions of equimolar quantities of 2.2'-dihydroxybiphenyi (1) with trichloromethylphosphonic dichloride (2a), O-2-chloroethyi phosphoryldichloride (2b) and dichlorophosphinyl carbamates (5a-c) at 45-50°C for (3a & 3b) and 40-45°C for (6a-c) in dry toluene in the presence of tnethylamme. Elemental. IR and NMR (*H & "P) data have been discussed and supported all structures. Brought to you by | University of California Authenticated Download Date | 6/7/15 5:03 AM Vol. 7, No. 3, 2001 Synthesis and characterization of 6-substituted dibenzo[d,J][1,3,2Jdioxa phosphepin 6-oxides Brought to you by | University of California Authenticated Download Date | 6/7/15 5:03 AM Vol. 7, No. 3, 2001 Synthesis and characterization of 6-substituted dibenzo [dJ] [1,3,2]dioxa phosphepin 6-oxides solution of 1 (1.86 g, 0.01 mol) and triethylamine (2.02 g, 0.02 mol) in dry toluene (50 mL). When the addition was complete, the mixture was stirred and allowed to warm slowly to 40-45°C and maintained at this temperature for 7 hours. The completion of the reaction was monitored by TLC analysis. The solid triethylamine hydrochloride was filtered off and the solvent was evaporated under reduced pressure. The gummy residue was washed with water, dried and treated with 2-propanol. A white solid obtained after recrystallization of the crude product from 2-propanol afforded 6b, yield 0.192 g (60%), mp 250-252°C. Physical and spectral data of 6a-c are given in tables 1-2.

A FACILE SYNTHESIS, SPECTRAL (IR, 1H, 13C & 31P NMR) CHARACTERISTICS AND ANTIMICROBIAL ACTIVITY OF 6-ARYLOXY/ARYLTHIO/ALKYLAMINO DIBENZO [d,f] [1,3,2]-DIOXAPHOSPHEPIN 6-SULFIDES

“…Table 2 contains the 'H NMR chemical shifts for 4a-k and 31 P NMR data for some of the compounds. The proton NMR spectra showed complex multiplets at δ 7.18-8.31 for aromatic protons of dibenzodioxaphosphepin system in 4a-k and 6-aryloxy/arylthio moieties in 4a-i 8 ' 9 . The distinction of the signals for the protons of dibenzodioxaphosphepin moiety and 6-aryloxy/arylthio moiety could not be made due to their identical environment.…”