4
4.
a) Tanabe, A.; Nakashima, H.; Yoshida, O.; Yamamoto, N.; Tenmyo, O.;
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(m, 3H), 7.51–7.56 (m, 2H), 7.64 (d, J = 7.8 Hz, 3H), 7.70 (t, J = 7.8 Hz,
3H), 8.02 (d, J = 8.4 Hz, 2H) ppm.13C NMR(CDCl3, 75 MHz) δ 122.7,
122.9, 126.5, 127.0, 127.1, 127.3, 127.6, 128.3, 129.0, 129.5, 129.9,
130.7, 131.1, 133.2, 135.7, 135.8, 137.2, 138.2, 199.4 ppm. HRMS:
calcd. for C27H19O [M+H] 358.1358; found 358.1354.
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15.
Representative experimental procedure for the preparation of
phenanthrene (ꢁa):
Compound 1a (179 mg, 0.5 mmol) was taken in a 10 mL round bottom
flask containing 3 mL of dry nitromethane and fitted with CaCl2 gurd
tube. Anhydrous Fe(OTf)3 (5.50 mg, 0.01 mmol) was added to it and
the reaction mixture was stirred for 2h at room temperature. After
completion of the reaction (TLC), nitromethane was distilled out
under reduced pressure and the residue was purified by silica gel
(mesh 100-200) column chromatography (petroleum ether/EtOAc) to
1
afford ꢁa (170 mg, 0.48 mmol, 95 %) as a white solid. m.p. 144 0C. H
NMR (CDCl3, 300 MHz): δ 7.10 (brs, 2H), 7.22–7.26 (m, 3H), 7.40–7.45