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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 4
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Original Articles

A One-Pot Generation of α-Chloro-α-Lithio Alkanephosphonates. A New Preparative Route to 1,2-Epoxyalkanephosphonates

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Pages 649-655 | Received 17 Sep 1991, Published online: 24 Sep 2006

References

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  • Griffin , C. E. and Kundu , S. K. 1969 . J. Org. Chem. , 34 : 1532
  • Sturtz , G. , Kahan , J. S. , Cassidy , P. J. and Kropp , H. 1974 . Ann. N.Y. Acad. Sci , 24 : 364
  • Hendlin , D. , Stapley , E. O. , Jackson , M. , Wallick , H. , Miller , A. K. , Wolf , F. J. , Miller , T. W. , Kahan , F. M. , Foltz , E. L. , Woodruff , H. B. , Mata , J. M. , HemanDez , S. and Mochales , S. 1969 . Science , : 122
  • Hirsch , E. , Hunig , S. and Reißig , H. U. 1982 . Chem. Ber. , 115 : 339 The chlorinations with benzenesulfonyl chloride as a chlorenium ion source have been reported. a), b) idem, 1982, 115, 3687; c) Lee, K., Shin, W. S., and Oh, D. Y., Synthetic Commun., in press
  • Corey , E. J. and Shulman , J. I. 1970 . J. Org. Chem. , 35 : 777 All compounds gave satisfactory spectral data. Run 2; 1H NMR (CDC13) δ 1.23–1.40 (6H, m),1.76 (3H, s), 4.00–4.73 (4H, m), 5.05–5.30 (1H, m), 7.27 (4H, m); IR (film) 1230 (P=O) cm−1; Mass (70 eV) m/z (%) 304 (M+, 1.7),77 (100.0), Run 3; 1H NMR (CDC13) δ 1.05–1.70 (9H, m),3.40 (1H, t), 3.75–4.30 (4H, m), 6.40–7.40 (7H, m); IR (film) 1254 (P=0) cm−1; Mass (70 eV) m/z (%) 296 (M+, 3.3),115 (100.0), Run 4; 1H NMR (CDCl3) δ 0.91–1.82 (22H, m), 4.17 (5H, m); IR (film) 1246 (P=O) cm-1, Run 5; 1H NMR (CDCl3) δ 1.00–1.61 (9H, m), 3.34–4.33 (6H, m). 7.17–7.80 (10H. m); IR (film) 1254 (P=O) cm-1, Run 6; 1H NMR (CDCl3) δ 0.97–1.77 (9H, m), 2.04 (3H, d), 4.00–4.60 (4H. m), 7.22 (5H, s); IR (film) 1230 (P=O) cm-1; Mass (70eV) m/z (%) 284 (M+.0.7), 121 (100.0), Run 7: 1H NMR (CDCl3) δ 0.88–2.30 (11H, m), 3.93 (3H, s), 4.04–4.63 (4H, m), 4.87–5.23 (1H, m), 6.83–7.67 (4H, m); IR (film) 1244 (P-O) cm-1; Mass (70 eV) m/z (%) 314 (M+,2.9),121 (100.0), Run 8; 1H NMR (CDCl3) δ 0.90–2.62 (11H, m), 3.47–4.50 (4H, m), 7.20–7.83 (10H, m); IR (film) 1240 (P=O) cm-1, Run 9; 1H NMR (CDCl3) δ 1.21–1.43 (6H, m), 4.02–4.70 (4H, m), 5.02–5.31 (1H, m), 7.30 (10H, m); IR (film) 1240 (P=O) cm−1

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