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M. Honda et al. / Tetrahedron 65 (2009) 9403–9411
326.1136; 1H NMR (CDCl3)
d
7.29–7.18 (m, 5H), 6.08 (s, 1H), 3.37 (dq,
0.83 (d, J¼7.3 Hz, 3H); 13C NMR (CDCl3)
d 149.9, 133.8, 133.6, 132.5,
128.9, 128.2, 127.7, 127.3, 127.2, 126.0, 42.1, 39.3, 13.9, 13.3.
J¼6.1, 5.8 Hz,1H), 3.28 (s, 3H), 2.14 (dq, J¼7.3, 5.8 Hz,1H),1.24 (s, 9H),
1.08 (d, J¼6.1 Hz, 3H),1.02 (d, J¼7.3 Hz, 3H); 13C NMR (CDCl3)
d 145.6,
132.5, 132.1, 131.5, 128.8, 126.4, 79.9, 57.3, 49.0, 33.8, 30.9, 176, 16.2.
4.3.11. cis-3,4-Dimethyl-1-tert-butyl-2-phenylselenocyclobut-1-ene
(3d). A pale yellow oil, IR (neat) 3055, 2957, 2923, 2857, 1574, 1475,
1433, 1025, 739 cmꢂ1; HRMS calcd for C16H22Se (Mþ) 294.0887,
4.3.3. 4-Methoxy-3-methyl-1-phenyl-2-phenylselenopent-1-ene
(2c). A pale yellow oil, IR (neat) 3057, 3026, 2952, 1577, 1475, 1436,
1101, 736 cmꢂ1; HRMS calcd for C19H22OSe (Mþ) 346.0836, found
found 294.0871; 1H NMR (CDCl3)
d 7.50–7.15 (m, 5H), 3.01 (dq,
J¼7.1, 4.7 Hz, 1H), 2.16 (dq, J¼7.1, 4.7 Hz, 1H), 1.16 (s, 9H), 1.07 (d,
346.0821; 1H NMR (for Z-isomer, CDCl3)
d 7.45–7.14 (m,10H), 6.79 (s,
J¼7.1 Hz, 3H), 0.72 (d, J¼7.1 Hz, 3H).
1H), 3.66 (dq, J¼6.3 Hz, 5.4 Hz, 1H), 3.07 (s, 3H), 2.81–2.70 (m, 1H),
1.12 (d, J¼7.1 Hz, 3H), 1.08 (d, J¼6.3 Hz, 3H); 1H NMR (for E-isomer,
4.3.12. 4-Butyl-1-phenyl-2-phenylselenocyclobut-1-ene (3e). A pale
yellow oil, IR (neat) 3050, 2958, 2920, 2856, 1575, 1474, 1432, 1021,
738 cmꢂ1; HRMS calcd for C20H22Se (Mþ) 342.0887, found 342.0871;
CDCl3)
d 7.35–7.16 (m, 10H), 6.79 (s, 1H), 3.50–3.41 (m, 1H), 3.24 (s,
3H), 3.20–3.12 (m, 1H), 1.14 (d, J¼6.1 Hz, 3H), 1.08 (d, J¼6.9 Hz, 3H).
1H NMR (CDCl3)
d
7.44–7.13 (m, 5H), 3.22–3.15 (m, 1H), 2.65 (dd,
J¼13.5, 4.5 Hz, 1H), 2.14 (dd, J¼13.5, 1.6 Hz, 1H), 1.31–1.29 (m, 5H),
0.89–0.84 (m, 4H); 13C NMR (CDCl3)
148.8,134.1,134.0,128.9,128.2,
4.3.4. 6-Methoxy-2,2,5-trimethyl-4-phenylselenohept-3-ene (2d). A
pale yellow oil, IR (neat) 3062, 3017, 2947, 1576, 1475, 1432, 1103,
d
732 cmꢂ1
;
HRMS calcd for C17H26OSe (Mþ) 326.1149, found
127.5, 126.9, 125.7, 125.6, 124.7, 41.6, 38.3, 32.8, 29.3, 22.9, 14.2.
326.1134; 1H NMR (CDCl3)
d 7.43–7.16 (m, 5H), 6.07 (s, 1H), 3.64 (dq,
J¼6.4, 4.7 Hz, 1H), 3.08 (s, 3H), 2.55 (dq, J¼7.1, 4.7 Hz, 1H), 1.25 (s,
4.3.13. r-2-Phenyl-t-3,c-4-dimethylcyclobutanone (4a). A pale yel-
low oil, IR (neat) 3054, 2960, 2928, 2858, 1778, 1716, 1683, 1456,
1436, 1072, 740 cmꢂ1; HRMS calcd for C12H14O (Mþ) 174.1045,
9H), 0.98 (d, J¼6.4 Hz, 3H), 0.94 (d, J¼7.1 Hz, 3H).
4.3.5. 4-Methoxy-1-phenyl-2-phenylselenooct-1-ene (2e). A pale
found 174.1049; 1H NMR (CDCl3)
d 7.35–7.11 (m, 5H), 3.95 (dd,
yellow oil, IR (neat) 3062, 3023, 2955, 1575, 1473, 1432, 1104,
J¼8.9, 2.3 Hz, 1H), 2.96–2.90 (m, 1H), 2.18–2.04 (m, 1H), 1.49 (d,
739 cmꢂ1
;
HRMS calcd for C21H26OSe (Mþ) 374.1149, found
J¼6.4 Hz, 3H), 1.20 (d, J¼7.2 Hz, 3H).
374.1135; 1H NMR (CDCl3)
d 7.52–7.18 (m, 10H), 6.95 (s, 1H), 3.41 (m,
1H), 3.14 (s, 3H), 2.61 (dd, J¼14.0, 6.4 Hz, 1H), 2.32 (dd, J¼14.0,
4.3.14. 3-Butyl-2-phenylcyclobutanone (4e). A colorless oil, IR
6.3 Hz, 1H), 1.46–1.15 (m, 6H), 0.88–0.83 (m, 3H); 13C NMR (CDCl3)
(neat) 3062, 2957, 2920, 2867, 1770, 734 cmꢂ1; HRMS calcd for
d
137.3, 134.1, 133.3, 132.0, 128.9, 128.8, 128.7, 127.8, 127.0, 79.6, 57.0,
C14H18O (Mþ) 202.1358, found 202.1355; 1H NMR (CDCl3)
d 7.48–
44.0, 33.3, 27.5, 22.8, 12.1.
7.14 (m, 5H), 4.04 (dt, J¼7.8, 2.2 Hz, 1H), 3.11 (ddd, J¼11.0, 8.7,
2.3 Hz, 1H), 2.59–2.49 (m, 1H), 1.91–1.83 (m, 1H), 1.77–1.70 (m, 1H),
1.41–1.20 (m, 5H), 1.39–1.42 (m, 4H), 0.90 (t, J¼7.1 Hz, 3H).
4.3.6. 4-Methoxy-1,4-diphenyl-2-phenylselenobut-1-ene (2g). A pale
yellow oil, IR (neat) 3063, 3025, 2945, 1576, 1477, 1433, 1101,
736 cmꢂ1
;
HRMS calcd for C23H22OSe (Mþ) 394.0836, found
4.3.15. 2-tert-Butyl-3-butylcyclobutanone (4f). A colorless oil, IR
394.0824; 1H NMR (for Z-isomer, CDCl3)
d
7.37–7.11 (m, 15H), 6.77 (s,
(neat) 2955, 2916, 2855, 1780, 739 cmꢂ1; HRMS calcd for C12H22
O
1H), 4.43 (dd, J¼7.9, 5.6 Hz, 1H), 3.18 (s, 3H), 2.82 (dd, J¼14.2, 7.9 Hz,
(Mþ) 182.1671, found 182.1670; 1H NMR (CDCl3)
8.6, 2.6 Hz, 1H), 2.63 (ddd, J¼9.9, 6.4, 3.3 Hz, 1H), 2.46(ddd, J¼17.6,
6.4, 3.6 Hz, 1H), 2.24–2.09 (m, 1H), 1.78–1.65 (m, 1H), 1.52–1.41 (m,
1H), 1.39–1.42 (m, 4H), 0.96 (s, 9H), 0.94–0.87 (m, 3H).
d
2.89 (ddd, J¼17.6,
1H), 2.56 (dd, J¼14.2, 5.6 Hz, 1H); 1H NMR (for E-isomer, CDCl3)
d
7.33–7.16 (m, 15H), 7.00 (s, 1H), 4.60 (dd, J¼8.9, 4.8 Hz, 1H), 3.19 (s,
3H), 3.14 (dd, J¼14.5, 8.9 Hz, 1H), 2.56 (dd, J¼14.5, 4.8 Hz, 1H).
4.3.7. trans-3,4-Dimethyl-1-phenyl-2-phenylselenocyclobut-1-ene
(3a). A pale yellow oil, IR (neat) 3057, 2955, 2922, 2854, 1577, 1475,
1437, 1022, 738 cmꢂ1; HRMS calcd for C18H18Se (Mþ) 314.0574,
4.3.16. 1-Phenyl-1-phenylselenopentan-3-one (5a). A pale yellow
oil, IR (neat) 3055, 2972, 2925, 1703, 1577, 1474, 1109, 1021,
731 cmꢂ1
;
HRMS calcd for C17H18OSe (Mþ) 318.0523, found
found 314.0555; 1H NMR (CDCl3)
d
7.58–7.18 (m, 10H), 2.77 (dq,
318.0525; 1H NMR (CDCl3)
d
7.41–7.09 (m, 10H), 4.81 (dd, J¼8.4,
J¼6.7, 1.2 Hz, 1H), 2.47 (dq, J¼6.7, 1.2 Hz, 1H), 1.32 (d, J¼6.7 Hz, 3H),
6.6 Hz,1H), 3.18 (dd, J¼17.0, 8.4 Hz,1H), 3.04 (dd, J¼16.9, 6.6 Hz,1H),
0.95 (d, J¼6.7 Hz, 3H); 13C NMR (CDCl3)
d
148.6, 134.0, 133.3, 129.5,
2.28 (m, 1H), 0.92 (t, J¼7.3 Hz, 3H); 13C NMR (CDCl3)
d 207.9, 141.3,
128.9, 128.3, 128.4, 127.2, 127.1, 125.9, 47.5, 44.9, 17.7, 17.2.
135.3, 128.7, 128.6, 128.1, 127.8, 127.3, 126.8, 48.2, 41.7, 36.5, 7.4.
4.3.8. trans-3,4-Dimethyl-1-tert-butyl-2-phenylselenocyclobut-1-
4.3.17. 1-Phenyl-1-phenylselenohexan-3-one (5b). A pale yellow oil,
IR (neat) 3054, 2970, 2928, 1705, 1578, 1476, 1112, 738 cmꢂ1; HRMS
calcd for C18H20OSe (Mþ) 332.0679, found332.0663;1H NMR (CDCl3)
ene (3b). A pale yellow oil, IR (neat) 3056, 2956, 2924, 2856, 1579,
1473, 1436, 1021, 739 cmꢂ1
;
HRMS calcd for C16H22Se (Mþ)
294.0887, found 294.0872; 1H NMR (CDCl3)
d
7.50–7.13 (m, 5H),
d
7.40–7.09 (m, 10H), 4.80 (dd, J¼8.4, 6.4 Hz, 1H), 3.18 (dd, J¼17.0,
2.38 (dq, J¼6.8, 1.4 Hz, 1H), 2.16 (dq, J¼6.8, 1.4 Hz, 1H), 1.20 (d,
8.4 Hz, 1H), 3.03 (dd, J¼17.0, 6.4 Hz, 1H), 2.24 (dt, J¼7.4, 4.1 Hz, 1H),
J¼6.8 Hz, 3H), 1.16 (s, 9H), 0.85 (d, J¼6.8 Hz, 3H).
1.47 (m, 2H), 0.78 (t, J¼7.4 Hz, 3H); 13C NMR (CDCl3)
d 207.6, 141.3,
135.3, 128.7, 128.6, 128.1, 127.8,127.3,126.8, 48.6, 45.2, 41.7, 168,13.5.
4.3.9. trans-3-tert-Butyl-2,3-dimethyl-4-phenylselenocyclobut-1-ene
(3b0). A pale yellow oil, IR (neat) 3055, 2956, 2923, 2856, 1575,
1475, 1433, 1020, 739 cmꢂ1; HRMS calcd for C16H22Se (Mþ)
4.3.18. 5-Methyl-1-phenyl-1-phenylselenohexan-3-one (5c). A pale
yellow oil, IR (neat) 3056, 2972, 2925, 1704, 1576, 1473, 1109, 1018,
294.0887, found 294.0870; 1H NMR (CDCl3)
d
7.50–7.13 (m, 5H),
739 cmꢂ1 HRMS calcd for C19H22OSe (Mþ) 346.0836, found
;
2.60–2.52 (m, 1H), 2.24–2.23 (m, 1H), 1.64 (q, J¼1.2 Hz, 3H), 1.13 (d,
346.0823; 1H NMR (CDCl3)
d
7.40–7.12 (m, 10H), 4.80 (dd, J¼8.4,
J¼8.5 Hz, 3H), 0.87 (s, 9H).
6.4 Hz,1H), 3.18 (dd, J¼17.0, 8.5 Hz,1H), 3.01 (dd, J¼17.0, 6.4 Hz,1H),
2.15 (d, J¼7.8 Hz, 1H), 2.15 (d, J¼5.8 Hz, 1H), 2.02 (dd, J¼7.7, 6.3 Hz,
4.3.10. cis-3,4-Dimethyl-1-phenyl-2-phenylselenocyclobut-1-ene
(3c). A pale yellow oil, IR (neat) 3055, 2956, 2923, 2856, 1577, 1476,
1438, 1021, 736 cmꢂ1; HRMS calcd for C18H18Se (Mþ) 314.0574,
1H), 0.78 (d, J¼6.4 Hz, 6H); 13C NMR (CDCl3)
d 207.3, 141.3, 135.3,
128.7, 128.6, 128.1, 127.8, 127.3, 126.8, 51.3, 41.6, 24.2, 22.4, 22.3.
found 314.0558; 1H NMR (CDCl3)
d
7.58–7.09 (m, 10H), 3.40 (dq,
4.3.19. 5,5-Dimethyl-1-phenyl-1-phenylselenohexan-3-one (5d). A
J¼7.0, 5.0 Hz, 1H), 3.06 (dq, J¼7.3, 5.0 Hz, 1H), 1.17 (d, J¼7.0 Hz, 3H),
pale yellow oil, IR (neat) 3054, 2970, 2926, 1703, 1577, 1472, 1107,