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CDCl3) 10.5, 125.6, 128.0, 130.4, 132.2, 136.1, 138.7, 142.1,
149.5, 195.0.
4.3.15. (E)-3-Furan-2-yl-2-ethylpropenal (10b)
Column flash chromatography was done using hexane/
ether (25/1) as eluent. Oil.
IR (CDCl3) 1670 cmꢀ1 (C@O), 1618 cmꢀ1 (C@C). Anal.
Calc. for C12H12O: C, 83.69; H, 7.02. Found: C, 83.56; H,
7.11%.
1H NMR (300 MHz, CDCl3) d 1.07 (t, 3H, J = 7.3 Hz,
CH3), 2.64 (q, 2H, J = 7.3 Hz, CH2), 6.56 (dd, 1H,
J = 3.3 Hz, J = 3.7 Hz, ArH-2), 6.77 (d, 1H, J = 3.7 Hz,
ArH-1), 6.93 (s, 1H, H-3), 7.62 (d, 1H, J = 3.3 Hz, ArH-
3), 9.45 (s, 1H, H-1); 13C NMR (75 MHz, CDCl3) 12.7,
18.1, 112.6, 116.5, 134.8, 141.1, 145.4, 151.2, 194.1.
IR (CDCl3) 1676 cmꢀ1 (C@O), 1632 cmꢀ1 (C@C). Anal.
Calc. for C9H10O2: C, 71.98; H, 6.71. Found: C, 71.68; H,
6.31%.
4.3.11. (E,E)-5-Furan-2-yl-2-methylpenta-2,4-dienal (16a)
Column flash chromatography was done using hexane/
ethyl acetate (90/10) as eluent. m.p.: 52 ꢁC (Lit 11: 50 ꢁC).
1H NMR (250 MHz, CDCl3) d 1.92 (s, 3H, CH3), 6.46
(d, 1H, J = 4.7 Hz, ArH-1), 6.51 (dd, 1H, J = 11.7 Hz,
J = 15.0 Hz, H-4), 6.74 (d, 1H, J = 15.0 Hz, H-5), 6.93
(d, 1H, J = 11.7 Hz, H-3), 7.00 (dd, 1H, J = 3.6 Hz,
J = 4.7 Hz, ArH-2), 7.09 (d, 1H, J = 3.6 Hz, ArH-3), 9.47
(s, 1H, H-1); 13C NMR (75 MHz, CDCl3) 9.6, 112.3,
112.8, 121.8, 127.2, 137.8, 145.3, 150.6, 152.3, 194.4.
IR (CDCl3) 1740 cmꢀ1 (C@O), 1650 cmꢀ1 (C@C). Anal.
Calc. for C10H10O2: C, 74.06; H, 6.21. Found: C, 74.1; H,
6.02%.
4.3.16. (E,E)-2-Ethylhexa-2,4-dienal (17b)
Column flash chromatography was done using hexane/
ether (23/1) as eluent. Oil.
1H NMR (300 MHz, CDCl3) d 0.99 (t, 3H, J = 7.7 Hz,
CH3), 1.94 (d, 3H, J = 6.9 Hz, CH3), 2.34 (q, 2H,
J = 7.7 Hz, CH2), 6.27 (m, 1H, H-5), 6.55 (dd, 1H,
J = 11.4 Hz, J = 16.2 Hz, H-4), 6.77 (d, 1H, J = 11.4 Hz,
H-3), 9.38 (s, 1H, H-1); 13C NMR (75 MHz, CDCl3)
13.7, 17.3, 19.1, 127.0, 140.7, 141.8, 149.0, 194.9.
IR (CDCl3) 1677 cmꢀ1 (C@O), 1637 cmꢀ1 (C@C). Anal.
Calc. for C8H12O: C, 77.38; H, 9.74. Found: C, 77.08; H,
9.14%.
4.3.12. (E,E)-2-Methylhexa-2,4-dienal (17a)
Column flash chromatography was done using hexane/
ethyl acetate (90/10) as eluent. Oil.
1H NMR (250 MHz, CDCl3) d 1.85 (s, 3H, CH3), 1.96
(d, 3H, J = 7.8 Hz, CH3), 6.28 (m, 1H, H-5), 6.56 (dd,
1H, J = 11.0 Hz, J = 16.4 Hz, H-4), 6.84 (d, 1H,
J = 11.0 Hz, H-3), 9.44 (s, 1H, H-1); 13C NMR
(62.9 MHz, CDCl3) 14.2, 25.9, 126.8, 134.8, 139.3, 148.1,
194.1.
4.3.17. (E)-a-Propylcinnamaldehyde (7c)
Column flash chromatography was done using hexane/
ether (23/1) as eluent. Oil.
1H NMR (300 MHz, CDCl3) d 0.98 (t, 3H, J = 7.3 Hz,
CH3), 1.51 (m, 2H, CH2b), 2.51 (t, 2H, J = 8.1 Hz,
CH2a), 7.21 (s, 1H, H-3), 7.38–7.51 (m, 5H, ArH), 9.54
(s, 1 H, H-1); 13C NMR (75 MHz, CDCl3) 14.2, 21.5,
26.6, 128.7, 129.4, 129.5, 134.9, 143.1, 149.8, 195.6.
IR (CDCl3) 1677 cmꢀ1 (C@O), 1623 cmꢀ1 (C@C). Anal.
Calc. for C12H14O: C, 82.72; H, 8.10. Found: C, 82.12; H,
8.01%.
IR (CDCl3) 1677 cmꢀ1 (C@O), 1637 cmꢀ1 (C@C). Anal.
Calc. for C7H10O: C, 76.33; H, 9.15. Found: C, 76.03; H,
9.01%.
4.3.13. (E)-2,5-Dimethylhexa-2,4-dienal (18a)
Column flash chromatography was done using hexane/
ethyl acetate (90/10) as eluent. Oil.
1H NMR (250 MHz, CDCl3) d 1.81 (s, 3H, CH3), 1.95
(s, 6H, 2CH3), 6.26 (d, 1H, J = 11.8 Hz, H-4), 7.07 (d,
1H, J = 11.8 Hz, H-3), 9.47 (s, 1H, H-1); 13C NMR
(75 MHz, CDCl3) 7.3, 17.1, 25.2, 119.3, 133.4, 143.2,
145.8, 193.3.
4.3.18. (E)-4-Methoxy-a-propylcinnamaldehyde (9c)
Column flash chromatography was done using hexane/
ether (23/10) as eluent. Oil.
1H NMR (300 MHz, CDCl3) d 0.99 (t, 3H, J = 7.3 Hz,
CH3), 1.52 (m, 2H, CH2b), 2.52 (t, 2H, J = 8.0 Hz,
CH2a), 3.84 (s, 3H, OCH3), 7.11 (s, 1H, H-3), 6.96 ; 7.48
(A2B2, 4H, J = 8.8 Hz, J = 8.8 Hz, ArH), 9.48 (s, 1H, H-
1); 13C NMR (75 MHz, CDCl3) 14.3, 21.4, 26.6, 55.3,
114.0, 127.6, 131.8, 140.9, 150.0, 160.8, 195.7.
IR (CDCl3) 1673 cmꢀ1 (C@O), 1602 cmꢀ1 (C@C). Anal.
Calc. for C13H16O2: C, 76.44; H, 7.90. Found: C, 76.02; H,
7.70%.
IR (CDCl3) 1680 cmꢀ1 (C@O), 1638 cmꢀ1 (C@C). Anal.
Calc. for C8H12O: C, 77.38; H, 9.74. Found: C, 77.18; H,
9.24%.
4.3.14. (E)-a-Ethylcinnamaldehyde (7b)
Column flash chromatography was done using hexane/
ether (23/1) as eluent. Oil.
1H NMR (300 MHz, CDCl3) d 1.14 (t, 3H, J = 7.7 Hz,
CH3), 2.56 (q, 2H, J = 7.7 Hz, CH2), 7.20 (s, 1H, H-3),
7.39–7.52 (m, 5H, ArH), 9.54 (s, 1H, H-1); 13C NMR
(75 MHz, CDCl3) 12.8, 18.0, 128.3, 128.8, 129.6, 134.9,
144.4, 149.5, 195.5.
4.3.19. (E)-2-Propyl-3-thiophen-2-propenal (11c)
Column flash chromatography was done using hexane/
ether (21/1) as eluent. Oil.
IR (CDCl3) 1679 cmꢀ1 (C@O), 1626 cmꢀ1 (C@C). Anal.
Calc. for C11H12O: C, 82.46; H, 7.55. Found: C, 82.16; H,
7.35%.
1H NMR (300 MHz, CDCl3) d 1.01 (t, 3H, J = 7.3 Hz,
CH3), 1.49 (m, 2H, CH2b), 2.58 (t, 2H, J = 8.1 Hz,
CH2a), 7.15 (dd, 1H, J = 5.1 Hz, J = 5.1 Hz, ArH-2),