J. CHEM. RESEARCH (S), 1999 443
4
5
6
P. E. Fanat, Chem. Rev., 1964, 64, 613.
biphenyl was obtained from this reaction. This observation
shows the possibility of formation of biarylmercury during
the reaction.
O. C. Dermer and M. T. Edmison, Chem. Rev., 1957, 57, 77.
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7
8
9
(a) A. McKillop, A. G. Turrell, D. W. Young and E. C.
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S. A. Deiko, A. K. Yatsimirsky and I. V. Berezin, Tetrahedron
Lett., 1981, 22, 3793.
(a) For a review see, I. V. Kozhenvikov and K. I. Matveev,
Usp. Khim.(Russ.), 1978, 47, 1231; (b) M. O. Unger and
R. A. Fouty, J. Org. Chem., 1968, 34, 18; (c) D. H. R. Barton,
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Experimental
Products were characterised by comparison of their physical data
with those of known samples. All yields refer to isolated products.
IR spectra were recorded on Perkin-Elmer 781 and Pye Unicam 8725
spectrometers and NMR spectra on a Bruker DPX 250.
Coupling of Toluene with Hg(OAc)2 and CPN: Typical Pro-
cedure.öA sealed tube containing 1 mmol of toluene, 1 mmol of
Hg(OAc)2, and 1 mmol of CPN was heated at 100 8C for 4 h in
an oil-bath. After cooling the tube, it was opened and chloroform
was added. The reaction mixture was washed with water several
times to remove any pyridine and pyridinium acetate which are
formed during the reaction. The organic solution was dried with
Na2SO4 and evaporated. Chromatography of the crude product on
silica gel eluted with n-hexane^CH2Cl2 ꢀ6 : 1 gave the pure bitolyl in
80% yield, mp 122 8C (lit.,7b 123 124 8C).
10 J. Yamashita, Y. Inoue, T. Kondo and H. Hashimoto, Chem.
Lett., 1986, 407.
11 A. Jutand and A. Mosleh, Synlett, 1993, 569.
12 M. Miura, H. Hashimoto, K. Itoh and M. Nomura, Chem.
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13 S. K. Kang, E. Y. Namkoong and T. Yamagichi, Synth. Com-
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14 S. K. Kang, U. Shivkumar, C. Ahn, C. A. Sang-Chul Choi and
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15 S. K. Kang, H. C. Ryu and H. J. Son, Synlett, 1997, 771.
16 J. C. Smith, Synthesis, 1984, 629.
We are grateful to Shiraz University Research Council for
partial support of this work.
Received, 6th January 1999; Accepted, 26th March 1999
Paper E/9/00181F
17 H. Firouzabadi and N. Iranpoor, Synth. Commun., 1983, 13,
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18 (a) H. Firouzabadi, N. Iranpoor, G.H. Hajipoor, F.
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