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12
tert
-Butyl-dimethyl-{[(4
E
,6
E
,8
E
,12
E
)-pentadeca-4,6,8,12,14-pentaenyl]oxy}-silane (8)
A 9:1 mixture of inseparable E- and Z-isomers; R
f
= 0.63 (PE-Et2O, 9:1). IR (neat): 3012, 2927, 2855, 1651, 1603, 1253, 1100 cm-1. 1H NMR (400 MHz, C6D6): δ = 6.29 (dtd, J = 17.0, 10.2, 0.7 Hz, 1 H), 6.18-5.97 (m, 5 H), 5.62 (m, 1 H), 5.54 (dt, J = 14.5, 6.7 Hz, 2 H), 5.06 (d, J = 17.0 Hz, 1 H), 4.93 (d, J = 10.1 Hz, 1 H), 3.51 (t, J = 6.2 Hz, 2 H), 2.14 (td, J = 7.4, 7.1 Hz, 2 H), 2.05-1.99 (m, 4 H), 1.56 (tt, J = 7.6, 6.3 Hz, 2 H), 1.00-0.96 (m, 9 H), 0.06-0.03 (m, 6 H). 13C NMR (100 MHz, C6D6): δ = 137.6 (d), 134.4 (d), 134.0 (d), 133.2 (d), 132.0 (d), 131.7 (d), 131.6 (d), 131.5 (d), 131.4 (d), 115.2 (t), 62.5 (t), 32.5 (t), 32.8 (t), 32.7 (t), 29.5 (t), 26.1 (q), 18.5 (s), -5.2 (q). MS (EI): m/z = 322 (7) [M+], 275 (20), 265 (20), 133 (100), 67 (37). ESI-HRMS: m/z calcd for C21H36OSi + Na+: 355.2428; found: 355.2429.
13
tert
-Butyl-dimethyl-{[(4
E
,6
E
,8
E
)-tetradeca-4,6,8,12-tetraenyl]oxy}-silane (10)
R
f
= 0.53 (PE-Et2O, 98:2). IR (neat): 3013, 2928, 2856, 1641, 1101, 993 cm-1. 1H NMR (400 MHz, CDCl3): δ = 6.12-6.01 (m, 4 H), 5.81 (ddt, J = 17.1, 10.3, 6.4 Hz, 1 H), 5.72-5.61 (m, 2 H), 5.02 (ddd, J = 17.1, 3.4, 1.5 Hz, 1 H), 4.97 (m, 1 H), 3.61 (t, J = 6.4 Hz, 2 H), 2.21-2.11 (m, 6 H), 1.64-1.54 (m, 2 H), 0.91-0.87 (m, 9 H), 0.06-0.02 (m, 6 H). 13C NMR (100 MHz, CDCl3): δ = 138.2 (d), 134.0(d), 133.4 (d), 131.4 (d), 131.1 (d), 130.9 (d), 130.8 (d), 114.8 (t), 62.5 (t), 33.5 (t), 32.4 (t), 32.2 (t), 29.1 (t), 26.0 (q), 18.4 (s), -5.3 (q). MS (EI): m/z = 306 (6) [M+], 249 (74), 175 (10), 133 (87), 131 (46), 91 (100), 81 (11), 75 (96), 55 (14). ESI-HRMS: m/z calcd for C19H34OSi + Na+: 329.2271; found: 329.2271.
