CHROMENONE PHOSPHANYLIDENE AND CYCLOBUTYLIDENE DERIVATIVES
203
and the residue was chromatographed on silica gel using n-hexane/acetone (70: 30) as
eluent to give 27a or 27b, respectively.
◦
Compound 27a: Yellow crystals; yield 67%; mp 143–145 C. IR (ν, cm−1): 1663
1
(γ -pyrone carbonyl group), 1701 (cyclobutane carbonyl groups). H NMR (500.1 MHz,
CDCl3): δ = 3.89 (s, 3H, OCH3), 6.72 (s, 1H, 9-H), 6.75 (d, JHH = 2.3 Hz, 1H, 3-H of
furan ring), 7.34 (s, 1H, 7-H), 7.44 (d, JHH = 2.3 Hz, 1H, 2-H of furan ring), 7.45–7.62 (m,
15H, arom-H), 7.67 (s, 1H, CH C). 13C NMR (125.8 MHz, CDCl3): δ = 60.5 (OCH3),
94.2 (C-9), 105.3 (C-3), 142.6 (C-4), 145.6 (C-2), 147.3 (C-7), 152.0 (HC C), 156.1
1
(d, JPC = 92.4 Hz, C P), 176.0 (pyrone carbonyl ring), 179.3 (CH C), 189.98 (C O
cyclobutylidene), 190.02 (C O, cyclobutylidene). 31P NMR (202.4 MHz, CDCl3): δ =
21.7. Anal. Calcd. for C35H23O6P (570.53): C, 73.68; H, 4.06; P, 5.43. Found: C, 73.60; H,
3.99; P, 5.39%.
Compound 27b: Yellow crystals; yield 70%; mp 205 ◦C (sharp). IR (ν, cm−1): 1652
1
(γ -pyrone carbonyl group), 1710 (carbonyl group). H NMR (500.1 MHz, CDCl3): δ =
3.81 (s, 3H, OCH3), 4.01 (s, 3H, OCH3), 6.76 (d, JHH = 2.3 Hz, 1H, 3-H of furan ring),
7.33 (s, 1H, 7-H), 7.38 (d, JHH = 2.3 Hz, 1H, 2-H of furan ring), 7.55–7.63 (m, 15H,
arom-H), 7.64 (s, 1H, CH C). 13C NMR (125.8 MHz, CDCl3): δ = 61.0 (OCH3), 61.5
(OCH3), 105.9 (C-3), 124.4 (C-9), 146.0 (C-2), 147.2 (C-4), 148.7 (C-7), 151.0 (HC C),
1
154.7 (d, JPC = 97.3 Hz, C P), 177.2 (pyrone carbonyl ring), 180.5 (HC C), 189.8
(C O, cyclobutylidene), 191.4 (C O, cyclobutylidene). 31P NMR (202.4 MHz, CDCl3):
δ = 21.7. Anal. Calcd. for C36H25O7P (600): C, 72.00; H, 4.20; P, 5.16. Found: C, 72.01;
H, 4.30; P, 5.28%.
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