THE REACTION OF CHLOROPHOSPHATES WITH STRONG BASES - SYNTHESIS AND CHARACTERIZATION OF THE PHOSPHONATE SALTS

The reaction of (OCH2CMe2CH2O)P(O)Cl (1) with 1,8-diazabicyclo[5.4.0]u ndec-7-ene 7-ene (DBU) afforded the phosphonate salt [(OCH2CMe2CH2O)P( O)(DBU)](+)[Cl] (3); the X ray structure of this compound as a hydrate shows that the C-6 (labeled as Cl in Fig.1) of the DBU is connected t o the phosphorus. In an analogous manner the eight-membered ring compo und {CH2(4-Me-2-t-Bu-C6H2O)(2)}P(O)Cl (2) also afforded a phosphonate salt along with the pyrophosphate [{CH2(4-Me-2-t-Bu-C6H2O)(2)} P(O)](2 )O (5). By contrast, in the reaction of 1 with 1,5-Diazabicyclo[4.3.0] non-5-ene (DBN), N-methyl imidazole or 4-dimethylaminopyridine no phos phonate salt was observed; the pyrophosphate was found to be the end p roduct and could be isolated. (C) 1998 Elsevier Science Ltd. All right s reserved.