PREPARATION AND SYNTHETIC APPLICATION OF DIETHYL 2-OXO-1,1-DIFLUOROPHOSPHONATES

Authors
TSAI HJ
Citation
Hj. Tsai, PREPARATION AND SYNTHETIC APPLICATION OF DIETHYL 2-OXO-1,1-DIFLUOROPHOSPHONATES, Phosphorus, sulfur and silicon and the related elements, 122, 1997, pp. 247-259
Citations number
25
Journal title
Phosphorus, sulfur and silicon and the related elements → ACNP
ISSN journal
10426507
Volume
122
Year of publication
1997
Pages
247 - 259
Database
ISI
SICI code
1042-6507(1997)122:<247:PASAOD>2.0.ZU;2-S
Abstract
Reaction of diethyl(bromodifluoromethyl)phosphonate (EtO)(?)2P(O)CF2Br 1 with activated zinc gave [(diethoxyphosphonyl)difluoromethyl]zinc b romide (EtO)(2)P(O)CF2ZnBr 2, which was acylated with various acylatin g agents to afford diethyl 2-oxo-1,1-difluorophosphonates (EtO)(2)P(O) CF2C(O)R 4 in good yields. Treatment of phosphonates 4 such as diethyl 2-oxo-1,1-difluoropropylphosphonate (EtO)(2)P(O)CF2C(O)CH3 4a, ethyl difluoro(diethoxyphosphonyl)pyruvate (EtO)(2)P(O)CF2C(O)CO2Et 4e and N ,N-diethyldifluoro(diethoxyphosphonyl)acetamide (EtO)(2)P(O)CF2C(O)NEt 2 4h with Grignard reagents R'MgX provided. 1,1-difluoroolefins R'(CH3 )C=CF2, R'(CO2Et)C=CF2 and R'(NEt2) C=CF2, respectively.