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HETEROCYCLES, Vol. 86, No. 1, 2012
128.3, 128.4, 134.3, 141.0, 149.6, 217.9; MS (FAB) m/z 367 (M++H).
3e: pale yellow oil; Rf = 0.41 (20% EtOAc in hexane); IR (neat) 1742 cm-1; 1H NMR (300 MHz, CDCl3)
" 0.97 (3H, d, J = 6.7 Hz), 1.60 (1H, m), 1.93 (1H, m), 2.00 (1H, m), 2.19 (1H, m), 2.38 (1H, m), 2.42
(2H, td, J = 7.4 and 6.4 Hz), 2.74 (2H, t, J = 7.4 Hz), 2.96 (1H, tt, J = 12.1 and 6.7 Hz), 5.76 (1H, d, J =
13
15.6 Hz), 5.86 (1H, dt, J = 15.6 and 6.4 Hz), 6.33 (1H, s), 7.14-7.30 (5H, m); C NMR (75 MHz, CDCl3)
" 11.8, 24.3, 34.4, 35.3, 36.8, 48.2, 51.3, 78.6, 125.9, 127.1, 128.3, 128.4, 134.2, 141.0, 149.0, 218.9; MS
(FAB) m/z 381 (M++H).
1
3f: colorless oil; Rf = 0.19 (10% EtOAc in hexane); IR (neat) 1704 cm-1; H NMR (300 MHz, CDCl3) "
1.50 (1H, m), 1.63-1.79 (2H, m), 2.03-2.27 (4H, m), 2.36-2.45 (3H, m), 2.74 (2H, t, J = 7.4 Hz), 2.99 (1H,
tt, J = 12.4 and 4.0 Hz), 5.72-5.86 (2H, m), 6.17 (1H, s), 7.15-7.31 (5H, m); 13C NMR (75 MHz, CDCl3) "
25.1, 28.6, 34.4, 35.3, 40.9, 44.8, 45.9, 76.7, 125.9, 127.6, 128.3, 128.5, 134.0, 141.1, 150.5, 210.2; MS
(FAB) m/z 381 (M++H).
(3E)-2-Methyl-6-phenyl-1,3-hexadiene 12 The reaction was performed by the same method described
in the general procedure except quenching with 3 eq of acetic acid instead of iodine at rt. Crude product
was purified by chromatography on Al2O3 to give terminal diene in 93% yield. Yellow oil; Rf = 0.40
1
(hexane); H NMR (300 MHz, CDCl3) " 1.82 (3H, s), 2.41 (2H, td, J = 7.9 and 6.8 Hz), 2.72 (2H, t, J =
7.9 Hz), 4.87 (2H, s), 5.69 (1H, dt, J = 15.7 and 6.8 Hz), 6.17 (1H, d, J = 15.7 Hz), 7.15-7.30 (5H, m); 13C
NMR (75 MHz, CDCl3) " 18.7, 34.6, 36.0, 114.6, 125.8, 128.3, 128.4, 129.8, 133.4, 141.9, 142.0; MS
(EI) m/z (rel. intensity) 172 (M+, 49), 157 (25), 91 (base). HRMS (EI) m/z Calcd for C13H16 (M+) 172.1252.
Found 172.1242.
Isomerization conditions and formation of isomerized products. The reaction was conducted at 0 °C
in all the process including the addition of Bu3SnMgMe described above.
4: colorless oil; Rf = 0.31 (hexane); 1H NMR (300 MHz, CDCl3) " 1.93 (3H, s), 2.46 (2H, td, J = 7.8 and
7.3 Hz), 2.74 (2H, t, J = 7.8 Hz), 5.59 (1H, dt, J = 11.6 and 7.3 Hz), 5.90 (1H, d, J = 11.6 Hz), 6.04 (1H,
13
s), 7.16-7.30 (5H, m); C NMR (75 MHz, CDCl3) " 24.4, 31.0, 35.6, 77.7, 128.1, 128.3, 128.4, 131.0,
132.9, 141.6, 144.2; MS (EI) m/z (rel. intensity) 298 (M+, 36), 207 (12), 171 (38), 91 (base). HRMS (EI)
m/z Calcd for C13H15I (M+) 298.0219. Found 298.0232.
6: colorless oil; Rf = 0.38 (hexane); 1H NMR (300 MHz, CDCl3) " 1.86 (3H, s), 2.49 (2H, td, J = 7.6 and
7.3 Hz), 2.70 (2H, t, J = 7.6 Hz), 5.44 (1H, dt, J = 11.5 and 7.3 Hz), 5.82 (1H, d, J = 11.5 Hz), 5.93 (1H,
13
s), 7.15-7.32 (5H, m); C NMR (75 MHz, CDCl3) " 24.8, 30.5, 36.0, 77.2, 126.0, 128.4, 128.5, 130.1,
131.2, 141.4, 144.3; MS (EI) m/z (rel. intensity) 298 (M+, 7), 32 (base). HRMS (EI) m/z Calcd for C13H15I
(M+) 298.0219. Found 298.0205.
7: colorless oil; Rf = 0.32 (hexane); 1H NMR (300 MHz, CDCl3) " 1.93 (3H, s), 2.50 (2H, td, J = 8.0 and
6.8 Hz), 2.77 (2H, t, J = 8.0 Hz), 5.94 (1H, dt, J = 15.6 and 6.8 Hz), 6.00 (1H, s), 6.46 (1H, d, J = 15.6