Tetrahedron Letters

Fluoride ion induced Horner-Emmons reactions of α-silylalkylphosphonates with carbonyl compounds

T Kawashima, T Ishii, N Inamoto

Index: Kawashima, Takayuki; Ishii, Takafumi; Inamoto, Naoki Tetrahedron Letters, 1983 , vol. 24, # 7 p. 739 - 742

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Citation Number: 17

Abstract

1a was prepared in 92% yield by lithiation and silylation of 2a ; bp 90–92°C/0.05 Torr; 1 H-NMR (CDCl 3 ): δ 0.13 (s, 9H), 2.73 (d, J 2 P,H = 25Hz, 1H), 3.56 (d, J 3 P,H =11Hz, 3H), 3.68 (d, J 3 P,H =11Hz, 3H), and 7.1–7.4 (m, 5H); 31 P-NMR (CDCl 3 ) : δ p 31.4 ppm (from 85%-H 3 PO 4 ); Mass spectrum: m/e 272 (M + , 49%), 257 (43), 167 (33), 151 (96), and 105 (100); Elementary analysis: Found: C, 53.04; H, 7.80%. Calcd for C 13 H 21 O 3 PSi: C, 52.92; H, 7.77%.