3 N. C. Norman, Chemistry of Arsenic, Antimony and Bismuth,
In the reaction with the carbodiimide 8c, a solution of 8d
(596 mg, 5.0 mmol) and Ph3AsO (32 mg, 0.1 mmol) in benzene
(3 cm3) was heated under reflux for 2 h. The generation of 8c
was confirmed by its IR spectrum. This solution was sub-
sequently used for the reaction with a solution of 6 prepared
above.
Blackie Academic & Professional, London, Weinheim, New York,
Tokyo, Melbourne and Madras, 1998; H. Suzuki and Y. Matano,
Organobismuth Chemistry, Elsevier, Amsterdam, London, New
York, Oxford, Paris, Shannon and Tokyo, 2001.
4 R. Appel and D. Wagner, Angew. Chem., 1960, 72, 209.
5 G. Wittig and D. Hellwinkel, Chem. Ber., 1964, 97, 789.
6 H. Suzuki and T. Ikegami, J. Chem. Res. (S), 1996, 24.
7 H. Suzuki, C. Nakaya, Y. Matano and T. Ogawa, Chem. Lett., 1991,
105.
Reaction of 4 with DMAD 17
8 S. V. Pasenok, N. V. Kirij, Y. L. Yagupolskii, D. Naumann and
W. Tyrra, J. Fluorine Chem., 1993, 63, 179.
9 T. Ikegami and H. Suzuki, Organometallics, 1998, 17, 1013.
10 Y. Matano, H. Nomura, M. Shiro and H. Suzuki, Organometallics,
1999, 18, 2580.
11 Yu. G. Gololobov and L. F. Kasukhin, Tetrahedron, 1992, 48, 1353.
12 S. Eguchi, Y. Matsushita and K. Yamashita, Org. Prep. Proced. Int.,
1992, 24, 209.
A solution of 4 (64 mg, 0.15 mmol) and DMAD 17 (101 mg,
0.75 mmol) in bromobenzene (3 cm3) was heated under reflux
for 20 h. After evaporation of the mixture, the residue was
purified by TLC on SiO2 (AcOEt) to give 23 (35 mg, 60%),
which is identical with the authentic specimen (Table 2, Entry
21).
13 M. Nitta, Rev. Heteroatom. Chem., 1993, 9, 87 and references cited
therein.
In situ preparation of 5 and reaction with DMAD 17
14 P. Molina and M. J. Vilaplana, Synthesis, 1994, 1197.
15 H. Wamhoff, G. Richardt and M. Stölben, Adv. Heterocycl. Chem.,
1995, 64, 159.
16 H. Yamamoto, M. Ohnuma and M. Nitta, J. Chem. Res. (S), 1999,
173; (M), 1999, 901.
17 Yu. G. Gololobov, I. N. Zhmurova and L. F. Kasukhin, Tetrahedron,
1981, 37, 437.
18 A. D. Beveridge and G. S. Harris, J. Chem. Soc. (A), 1964, 6076.
19 R. O. Day, J. M. Holmes, A. C. Sau, J. R. Devillers, R. R. Holmes
and J. A. Deiters, J. Am. Chem. Soc., 1982, 104, 2127; R. H. Fish and
R. S. Tannous, Organometallics, 1982, 1, 1238; C. A. Poutasse, R. O
Day, J. M. Holmes and R. R. Holmes, Organometallics, 1985, 4, 708;
R. R. Holmes, R. O. Day and A. C. Sau, Organometallics, 1985, 4,
714.
To a stirred solution of Ph3SbCl2 (212 mg, 0.5 mmol) and 7
(61 mg, 0.5 mmol) in bromobenzene (3 cm3) was added ButOK
(112 mg, 1.0 mmol) and the mixture was stirred for 30 min at rt.
To this solution was added a solution of DMAD 17 (711 mg,
5 mmol) in bromobenzene (2 cm3) and the mixture was heated
under reflux for 1 h. The reaction mixture was then filtered
through Celite, the filtrated was concentrated, and the residue
was purified by TLC on SiO2 (hexane–AcOEt 1 : 2) to give 23
(Table 2, Entry 22).
Crystal structure determination of 4‡
Single crystal of [C H ON᎐AsPh ] 4 were recrystallised from
᎐
7
5
3
20 A. Bondi, J. Phys. Chem., 1964, 68, 441.
AcOEt.
21 H. W. Roesky, M. Witt, W. Clegg, W. Isenberg, M. Noltemeyer and
G. M. Sheldrick, Angew. Chem., Int. Ed. Engl., 1980, 19, 943;
M. Witt, H. W. Roesky, M. Noltemeyer, W. Clegg, M. Schmidt and
G. M. Sheldrick, Angew. Chem., Int. Ed. Engl., 1981, 20, 974;
R. Bohra, H. W. Roesky, J. Lucas, M. Noltemeyer and G. M.
Sheldrick, J. Chem. Soc., Dalton Trans., 1983, 1011; H. W. Roesky,
N. Bertel, F. Edelmann, M. Noltemeyer and G. M. Sheldrick,
Z. Naturforsch., Teil B, 1988, 43, 72; K. Bailey, I. Gosney, R. O.
Gould, D. Lloyd and P. Taylor, J. Chem. Res. (S), 1988, 386; (M),
1988, 2950.
Crystal data. C25H20AsNO, M = 425.37, orthorhombic,
a = 25.5308(0), b = 28.5381(0), c = 10.7821(0) Å, V = 7855.86(0)
Å3, T = 298 K, space group Pcnb (no. 60), Z = 16, µ(Cu-
Kα) = 2.4413 mmϪ1, 8598 reflections measured, 7190 unique
(Rint = 0.019). The final R(F 2) and wR(F 2) were 0.067 and
0.080 for 6515 observed reflections [F 2 > 2σ(F 2)] used in all
calculations.33
22 J. March, Advanced Organic Chemistry: Reactions, Mechanisms, and
Structure, Wiley, New York, Chichester, Brisbane, Toronto and
Singapore, 4th edn., 1992, p. 21, Table 1.5.
23 A. Krebs and B. Schrader, Justus Liebigs Ann. Chem., 1967, 709, 46.
24 M. J. Barrow, O. S. Mills and G. Filippini, J. Chem. Soc., Chem.
Commun., 1973, 66.
25 A. D. Beverridge, G. S. Harris and F. Inglis, J. Chem. Soc. (A), 1966,
520.
26 G. Wittig and K. Clauss, Justus Liebigs Ann. Chem., 1952, 578, 136.
27 J. J. Monagle, J. Org. Chem., 1962, 27, 3851; P. Frøyen, Acta Chem.
Scand., 1969, 23, 2935.
Acknowledgements
Financial support from Waseda University Grants for Special
Research Projects is gratefully acknowledged. We also thank
the Materials Characterization Central Laboratory, Waseda
University, for technical assistance with spectral data, elemental
analyses, and X-ray structure analysis.
28 I. Ueda, M. Matsuo, K. Taniguchi, S. Shigenaga and T. Ogawara,
Jpn. Kokai Tokkyo Koho, JP 64 03,172 [89 03,172] (Chem. Abstr.,
1989, 111, 57734g).
29 I. Kawamoto, Y. Sugimura, N. Soma and Y. Kishida, Chem. Lett.,
1972, 931.
p1/b1/b103098c for crystallographic files in .cif or other electronic
format.
30 G. W. Brown, R. C. Cookson and I. D. R. Stevens, Tetrahedron Lett.,
1964, 1263; J. Barluenga, F. Lopez and F. Palacios, J. Chem. Soc.,
Perkin Trans. 1, 1989, 2273.
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