Phosphite to Phosphonate Rearrangement
2621
1
1P), 33.84 (s, 2P); H NMR(CDCl3)(300.08 MHz) δ 1.28 (s, 18 H), 1.35
(s, 36 H), 1.41 (s, 18 H), 1.44 (s, 36 H), 2.14 (dt, CH P( O),2JHCP
=
2
3
18.7 Hz, JHCCH = 8.0 Hz, 4 H), 2.56 (t, CH2N, 3JHCCH = 6.5 Hz, 2 H),
3
3
2.95 (dt, CH2N, JHCCP = 6.2; JHCCH = 8.0 Hz, 4 H), 3.74 (dt, CH2OP,
3JHCCH = 6.5 Hz, 3JHCOP = 8.0 Hz, 2 H), 7.16 (d, 4JHCCCH = 2.4 Hz, 4 H),
4
4
7.17 (d, JHCCCH = 2.4 Hz, 2 H), 7.40 (d, JHCCCH = 2.4 Hz, 2 H), 7.48
(unresolved dd, 4JHCCCH = 2.4 Hz, 4 H).
REFERENCES AND NOTES
[1] Presented in part at the 17th International Conf. on Adv. in Stabilization and Degra-
dation of Polymers; Luzern, Switzerland, June 12–14, 1995.
[2] (a) T. V. RajanBabu and A. L. Casalnuovo, J. Am. Chem. Soc., 114, 6265 (1992); (b) A.
Bendayan, H. Masotti, G. Peiffer, C. Siv, and A. J. Archavlis, Organomet. Chem., 444,
41 (1993). (c) A. L. Casalnuovo, T. V. RajanBabu, T. A. Ayers, and T. H. Warren, J.
Am. Chem. Soc., 116, 9869 (1994).
[3] (a) T. Higashizima, N. Sakai, K. Nozaki, and H. Takaya, Tetrahedron Lett., 35,
2023 (1994); (b) N. Sakai, K. Nozaki, K. Mashima, and H. Takaya, Tetrahedron
Asymmetry, 3, 583 (1994).
[4] (a) G. D. Cuny and S. L. Buchwald, J. Am. Chem. Soc., 115, 2066 (1993); (b) B.
Moasser, C. Gross, and W. L. Gladfelther, J. Organomet. Chem., 471, 201 (1994);
(c) B. Moasser and W. L. Gladfelther, Organometallics, 14, 3832 (1995).
[5] (a) E. Billig, A. G. Abatjoglou, and D. R. Bryant, U.S. Patent 4,748,261 (1988); Chem.
Abstr., 107, 7392 (1987). See also (b) J. E. Babin and G. T. Whiteker, U.S. Patent
5,360, 938 (1994); Chem. Abstr. 122, 186609 (1995).
[6] (a) G. J. H. Buisman, P. C. J. Kamer, and P. W. N. M. van Leeuwen, Tetrahedron:
Asymmetry, 4, 1625 (1993); (b) P. W. N. M. van Leeuwen, G. J. H. Buisman, A. van
Rooy, and P. C. J. Kamer, Recl. Trav. Chim. Pays-Bas., 113, 61 (1994); See also (c) T.
Jongsma, M. Fossen, G. Challa, and P. W. N. M. van Leeuwen, J. Molecular Cat., 83,
17 (1993); (d) A. van Rooy, E. N. A. Orij, P. C. J. Kamer, and P. W. N. M. van Leeuwen,
Organometallics, 14, 34 (1995); (e) G. J. H. Buisman, M. E. Martin, E. J. Vos, A.
Klootwijk, P. C. J. Kamer, and P. W. N. M. van Leeuwen, Tetrahedron: Asymmetry,
6, 719 (1995); (f) G. J. H. Buisman, L. A. van der Veen, A. Klootwijk, W. G. J. de
Lange, P. C. J. Kamer, P. W. N. M. van Leeuwen, and D. Vogt, Organometallics, 16,
2929 (1997); (g) L. A. van der Veen, P. H. Keeven, G. C. Shoemaker, J. N. H. Reek,
P. C. J. Kamer, P. W. N. M. van Leeuwen, M. Lutz, and A. L. Spek, Organometallics,
19, 872 (2000).
[7] (a) M. J. Baker, K. N. Harrison, A. G. Orpen, P. G. Pringle, and G. Shaw, J. Chem. Soc.,
Chem. Commun., 803 (1991); (b) R. B. Bedford, P. A. Chaloner Castillo`n, C. Claver,
E. Fernandez, R. B. Hitchcock, and A. Ruiz, Organometallics, 15, 3990 (1996); (c)
R. Kadyrov, D. Heller, and R. Selke, Tetrahedron: Asymmetry, 9, 329 (1998); (d) S.
Csere´pi-Szu´cs, I. To´th, L. Pa´rka´nyi, and J. Bakos, Tetrahedron: Asymmetry, 9, 3135
(1998); (e) M. Die´guez, A. Ruiz, and Claver, J. Org. Chem., 67, 3796 (2002), and
references therein.
[8] S. D. Pastor, J. S. Rogers, M. Ali NabiRahni, and E. D. Stevens, Inorg. Chem., 35,
2157 (1996).
[9] (a) S. D. Pastor, S. P. Shum, A. D. DeBellis, L. P. Burke, R. K. Rodebaugh, F. H.
Clarke, and G. Rihs, Inorg. Chem., 35, 949 (1996); (b) A. R. Smith, J. W. Bruno, and
S. D. Pastor, Phosphorus, Sulfur, Silicon Relat. Elem., 177, 479 (2002).