504
15
C. Ramesh et al.
PAPER
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IR: 2991, 1730 cm–1.
Catalysis with Organometallic Compounds, Vol. 1; VCH:
New York, 1996, 169. (b) Hayashi, M.; Takezaki, H.;
Hashimoto, Y.; Takaoki, K.; Saigo, K. Tetrahedron Lett.
1998, 39, 7529.
1H NMR: δ = 8.16 (d, 4 H, J = 17.2 Hz, Ar-H), 7.71 (d, 4 H, J = 17.2
Hz, Ar-H), 4.2 (q, 4 H, J = 8.2 Hz, OCH2), 1.3 (t, 6 H, J = 8.2 Hz,
CH3).
(4) (a) Tsuji, J. In Palladium Reagents and Catalysts; Wiley:
New York, 1999. (b) Hohn, A. In Applied Homogeneous
Catalysis with Organometallic Compounds, Vol. 1; VCH:
New York, 1996, 137. (c) Beller, M.; Tafesh, A. M. In
Applied Homogeneous Catalysis with Organometallic
Compounds, Vol. 1; VCH: New York, 1996, 187.
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1974, 39, 3318. (b) Schoenberg, A.; Heck, R. F. J. Org.
Chem. 1974, 39, 3327. (c) Hidai, M.; Hikita, T.; Wada, Y.;
Fujikura, Y.; Uchida, Y. Bull Chem. Soc. Jpn. 1975, 48,
2075. (d) Ito, T.; Mori Mizoroki, T.; Osaki, A. Bull. Chem.
Soc. Jpn. 1975, 48, 2091. (e) Stille, J. K.; Wong, P. K. J.
Org. Chem. 1975, 40, 532.
(6) (a) Tsuji, J. In Palladium Reagents and Catalysis; John
Wiley & Sons: Tokyo, 1995, 188–209. (b) Sugihara, T.;
Coperet, C.; Owczarczy, Z.; Haring, L. S.; Negishi, E. J. Am.
Chem. Soc. 1994, 116, 7923. (c) Grigg, R.; Sridharan, V.
Tetrahedron Lett. 1993, 34, 7471. (d) Harris, G. D.; Herr, R.
J.; Weinreb, S. J. Org. Chem. 1992, 2528. (e) Harris, G. D.;
Herr, R. J.; Weinreb, S. J. Org. Chem. 1993, 58, 5452.
(7) (a) Sugi, Y.; Takeuchi, K.; Hanaoka, T.; Matsuzaki, T.;
Takagi, S.; Doi, Y. J. Jpn. Pet. Inst. 1994, 37, 70.
(b) Kubota, Y.; Hanaoka, T.; Takeuchi, K.; Sugi, Y. Synlett
1994, 515–517. (c) Yoneyama, M.; Kakimoto, M.; Imai, Y.
Macromolecules 1988, 21, 1908.
16
IR: 1730 cm–1.
1H NMR: δ = 8.33 (d, 4 H, J = 18 Hz, Ar-H), 7.8 (d, 4 H, J = 18 Hz,
Ar-H), 7.48–7.42 (m, 4 H), 7.32–7.20 (m, 6 H).
Carbonylation-Polycondensation; General Procedure
In a typical procedure, 2,7-diiodo-9,10-dihydrophenanthene (2.5
mmol), bisphenol-A (2.5 mmol), Et3N (5.5 mmol) and 5% Pd/C (50
mg) in chlorobenzene (5 mL) were taken in autoclave (50 mL),
flushed 3 times with nitrogen, and pressurized with carbon monox-
ide (1.0 MPa). The autoclave was placed in oil bath pre-heated at
140–150 °C, and the whole reaction mixture was stirred for 6 h. Af-
ter the reaction, the autoclave was cooled, excess carbon monoxide
was purged, and the reaction mixture was filtered. The filtrate was
poured into MeOH (200 mL). Pale-yellow solid was filtered and
dried to afford poly [oxy-1,4-phenylene (1-methylethylidene)-1,4-
phenyleneoxycarbonyl (9,10-dihydro-2,7-phenanthrenediyl) carbo-
nyl]. All the products were characterized by IR and NMR. Molecu-
lar weight was determined by gel permeation chromatography using
polystyrene as a standard. Typical results are shown in Table 3.
1H NMR: δ = 8.17–8.05 (m, 4 H, Ar-H), 7.94–7.82 (m, 2 H, Ar-H),
7.20–7.0 (m, 8 H, Ar-H), 3.0 (s, 4 H, CH2), 1.73 (s, 6 H, CH3).
(8) (a) Yoneyama, M.; Kakimoto, M.; Imai, Y. Macromolecules
1989, 22, 2593. (b) Perry, R. J.; Tuner, S. R.; Blevins, R. W.
Macromolecules 1993, 26, 1509.
(9) (a) Kubota, Y.; Takeuchi, K.; Hanaoka, T.; Sugi, Y. Bull.
Chem. Soc. Jpn. 1994, 67, 563. (b) Kubota, Y.; Takeuchi,
K.; Hanaoka, T.; Sugi, Y. Catal. Today 1996, 31, 27.
(c) Kubota, Y.; Nakada, S.; Sugi, Y. Mat. Trans., JIM 2002,
43, 326.
Acknowledgment
C. Ramesh thanks the Ministry of Education, Culture, Sports, Sci-
ence, and Technology, Japan for the fellowship.
References
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Synthesis 2003, No. 4, 501–504 ISSN 0039-7881 © Thieme Stuttgart · New York