The reaction of chlorophosphates with strong bases: Synthesis and characterization of the phosphonate salts

✍ Scribed by M. Vijjulatha; K.Praveen Kumar; K.C. Kumara Swamy; J.J. Vittal

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 226 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)00096-3

✦ Synopsis

The reaction of (OCH2CMe2CH20)P(O)CI (l)with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afforded the phosphonate salt [(OCH2CMe2CH20)P(O)(DBU)]+[CI] (3); the X ray structure of this compound as a hydrate shows that the C-6 (labeled as C I in Fig. 1) of the DBU is c:onnected to the phosphorus. In an analogous manner the eight-membered ring compound {CH2(4-Me-2-t-Bu-C6H20)2}P(O)CI (2) also afforded a phosphonate salt along with the pyrophosphate [{CH2(4-Me-2-t-Bu-C6H20)2}P(O)]20 (5). By contrast, in the reaction of 1 with 1,5-Diazabicyclo[4.3.0}non-5-ene (DBN), N-methyl imidazole or 4dimethylaminopyridine no phosphonate salt was observed; the pyrophosphate was found to be the end product and could be isolated.