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33746885539
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Haszeldine, R.N.3
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37049100858
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Haszeldine, R.N.3
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0000756238
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Hanzawa, Y.; Kawagoe, K.-i.; Yamada, A.; Kobayashi, Y. Tetrahedron Lett. 1985, 26, 219.
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Hanzawa, Y.1
Kawagoe, K.-I.2
Yamada, A.3
Kobayashi, Y.4
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0025282413
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Burton, D. J.; Hartgraves, G. A.; Hsu, J. Tetrahedron Lett. 1990, 31, 3699.
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Burton, D.J.1
Hartgraves, G.A.2
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0034345661
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Konno, T.; Tanikawa, M.; Ishihara, T.; Yamanaka, H. Chem. Lett. 2000, 1360.
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28744431523
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Han, H. Y.; Kim, M. S.; Son, J. B.; Jeong, I. H. Tetrahedron Lett. 2006, 47, 209. Examples of fluorine-infstituted allenes:
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Han, H.Y.1
Kim, M.S.2
Son, J.B.3
Jeong, I.H.4
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13
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0000955664
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Examples of fluorine-infstituted allenes
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Dolbier, W. R. Jr.; Burkholder, C. R.; Piedrahita, C. A. J. Fluorine Chem. 1982, 20, 637.
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Dolbier Jr., W.R.1
Burkholder, C.R.2
Piedrahita, C.A.3
Mae, M.4
Hong, J.A.5
Xu, B.6
Hammond, G.B.7
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14
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69449088579
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72149133289
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Krause N.; Hashmi A. S. K., Eds.
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Modern Allene Chemistry, Vol. 1 and 2; Krause, N.; Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004.
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19
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0011301166
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Recent studies on bromoallenes
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Duggan, A.J.2
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52349108357
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21
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61349124101
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Braddock, D. C.; Bhuva, R.; Prez-Fuertes, Y.; Pouwer, R.; Robers, C. A.; Ruggiero, A.; Stokes, E. S. E.; White, A. J. P. Chem. Commun. 2008, 1419.
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Braddock, D.C.1
Bhuva, R.2
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Pouwer, R.4
Robers, C.A.5
Ruggiero, A.6
Stokes, E.S.E.7
White, A.J.P.8
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22
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68949131232
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3P has recently been reported, see: 2009
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3P has recently been reported, see:, Sakai N, Maruyama T, Konakahara T, Synlett 2009 2105
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Synlett
, pp. 2105
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Sakai, N.1
Maruyama, T.2
Konakahara, T.3
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25
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72149126616
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note
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Procedure for the Preparation of the Allenylcarbinols 7a and 7b To a solution of 3a (0.32 g, 1.20 mmol) and isobutyraldehyde (142 mL, 1.6 mmol) in Et2O (5 mL) was added BuLi (0.98 mL, 1.6 mmol, 1.6 M in hexane) at 105 C. The solution was stirred at that temperature for 2 h. The reaction mixture was quenched with 1 M aq HCl solution (3 mL) and extracted with EtOAc (3 20 mL). Usual workup and purification by silica gel chromatography (hexaneEtOAc, 12:1) afforded 7a (0.087 g, 0.41 mol 34%) and 7b (0.14 g, 0.66 mmol 55%). Compound 7a: colorless oil. Rf = 0.56 (hexaneEtOAc, 4:1). 1H NMR (300 MHz, CDCl3): d = 1.01 (d, J = 6.9 Hz, 6 H), 1.80 (br s, 1 H), 1.96 (oct, J = 6.6 Hz, 1 H), 4.12 (dd, J = 6.6, 1.5 Hz, 1 H), 6.73 (qd, J = 3.3, 1.5 Hz, 1 H), 7.267.38 (m, 5 H). 13C NMR (75.5 MHz, CDCl3): d = 17.0, 19.5, 32.7,73.8, 103.0, 106.0 (q, J = 32.3 Hz), 123.1 (q, J = 274.1 Hz), 127.4, 128.6, 129.0, 131.1, 204.4 (q, J = 4.4 Hz). 19F NMR (283 MHz, CDCl3): d = 62.44 (s). IR (neat): 692, 721, 747, 828, 920, 1001, 1029, 1074, 1127, 1210, 1273, 1369, 1387, 1411, 1462, 2874, 2934, 2963, 3429 cm1. HRMSFAB: m/z calcd for C14H16OF3 [M + H]+: 257.1153; found: 257.1176. Compound 7b: colorless oil. Rf = 0.47 (hexaneEtOAc, 4:1). 1H NMR (300 MHz, CDCl3): d = 1.00 (d, J = 6.6 Hz, 3 H), 1.01 (d, J = 6.6 Hz, 3 H), 1.88 (br s, 1 H), 1.96 (oct, J = 6.6 Hz, 1 H), 4.12 (dd, J = 6.6, 1.2 Hz, 1 H), 6.78 (qd, J = 3.3, 1.5 Hz, 1 H), 7.277.39 (m, 5 H). 13C NMR (75.5 MHz, CDCl3): d = 17.1, 19.6, 32.8, 73.6, 103.2, 106.1 (q,J = 32.2 Hz), 123.2 (q, J = 272.9 Hz), 127.6, 128.6, 129.0, 131.1, 204.1 (q, J = 4.3 Hz). 19F NMR (283 MHz, CDCl3): d = 62.52 (s). IR (neat): 692, 719, 747, 829, 920, 1000, 1029, 1074, 1123, 1210, 1274, 1369, 1388, 1411, 1462, 1715, 1961, 2876, 2933, 2967, 3036, 3410 cm1. HRMS FAB: m/z calcd for C14H16OF3 [M + H]+: 257.1153; found: 257.1187.
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26
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72149108933
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note
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Procedure for the Preparation of the Allenylcarbinols 7a and 7b To a solution of 3a (0.32 g, 1.20 mmol) and isobutyraldehyde (142 mL, 1.6 mmol) in Et2O (5 mL) was added BuLi (0.98 mL, 1.6 mmol, 1.6 M in hexane) at 105 C. The solution was stirred at that temperature for 2 h. The reaction mixture was quenched with 1 M aq HCl solution (3 mL) and extracted with EtOAc (3 20 mL). Usual workup and purification by silica gel chromatography (hexaneEtOAc, 12:1) afforded 7a (0.087 g, 0.41 mol 34%) and 7b (0.14 g, 0.66 mmol 55%). Compound 7a: colorless oil. Rf = 0.56 (hexaneEtOAc, 4:1). 1H NMR (300 MHz, CDCl3): d = 1.01 (d, J = 6.9 Hz, 6 H), 1.80 (br s, 1 H), 1.96 (oct, J = 6.6 Hz, 1 H), 4.12 (dd, J = 6.6, 1.5 Hz, 1 H), 6.73 (qd, J = 3.3, 1.5 Hz, 1 H), 7.267.38 (m, 5 H). 13C NMR (75.5 MHz, CDCl3): d = 17.0, 19.5, 32.7,73.8, 103.0, 106.0 (q, J = 32.3 Hz), 123.1 (q, J = 274.1 Hz), 127.4, 128.6, 129.0, 131.1, 204.4 (q, J = 4.4 Hz). 19F NMR (283 MHz, CDCl3): d = 62.44 (s). IR (neat): 692, 721, 747, 828, 920, 1001, 1029, 1074, 1127, 1210, 1273, 1369, 1387, 1411, 1462, 2874, 2934, 2963, 3429 cm1. HRMSFAB: m/z calcd for C14H16OF3 [M + H]+: 257.1153; found: 257.1176. Compound 7b: colorless oil. Rf = 0.47 (hexaneEtOAc, 4:1). 1H NMR (300 MHz, CDCl3): d = 1.00 (d, J = 6.6 Hz, 3 H), 1.01 (d, J = 6.6 Hz, 3 H), 1.88 (br s, 1 H), 1.96 (oct, J = 6.6 Hz, 1 H), 4.12 (dd, J = 6.6, 1.2 Hz, 1 H), 6.78 (qd, J = 3.3, 1.5 Hz, 1 H), 7.277.39 (m, 5 H). 13C NMR (75.5 MHz, CDCl3): d = 17.1, 19.6, 32.8, 73.6, 103.2, 106.1 (q,J = 32.2 Hz), 123.2 (q, J = 272.9 Hz), 127.6, 128.6, 129.0, 131.1, 204.1 (q, J = 4.3 Hz). 19F NMR (283 MHz, CDCl3): d = 62.52 (s). IR (neat): 692, 719, 747, 829, 920, 1000, 1029, 1074, 1123, 1210, 1274, 1369, 1388, 1411, 1462, 1715, 1961, 2876, 2933, 2967, 3036, 3410 cm1. HRMS FAB: m/z calcd for C14H16OF3 [M + H]+: 257.1153; found: 257.1187.
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27
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72149127580
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note
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Procedure for the Preparation of the 2,5-Dihydrofuran 8a To a solution of 7a (0.087 g, 0.41 mmol) in acetone (3 mL) was added AgNO3 (12 mg, 0.082 mmol) at r.t. The solution was protected from light and stirred at that temperature for 4 d. Concentration by rotary evaporator furnished a crude mixture that was purified by silica gel chromatography (hexaneEtOAc, 20:1) to afford 8a (0.066 g, 75%) as a pale yellow oil; Rf = 0.77 (hexaneEtOAc, 4:1). 1H NMR (300 MHz, CDCl3): d = 0.94 (d, J = 6.9 Hz, 3 H), 1.13 (d, J = 6.9 Hz, 3 H), 2.03 (septd, J = 6.6, 1.2 Hz, 1 H), 5.18 (dq, J = 6.6, 0.9 Hz, 1 H), 5.835.88 (m, 1 H), 6.45 (sext, J = 1.8 Hz, 1 H), 7.267.44 (m, 5 H). 13C NMR (75.5 MHz, CDCl3): d = 14.5, 19.9, 32.0, 87.7 (q, J = 0.6 Hz), 89.3 (q, J = 0.6 Hz), 121.7 (q, J = 269.2 Hz), 126.4, 128.4, 128.7, 131.9 (q, J = 33.5 Hz), 135.8 (q, J = 4.4 Hz), 140.0. 19F NMR (283 MHz, CDCl3): d = 64.13 (s). IR (neat): 698, 726, 760, 879, 917, 1009, 1051, 1068, 1126, 1158, 1242, 1265, 1281, 1334, 1360, 2876, 2935, 2970 cm1. HRMSFAB: m/z calcd for C14H16OF3 [M]+: 256.1075; found: 256.1046.
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