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7. All novel compounds were fully characterised (including
by high field 1H and 13C NMR spectroscopy and high-
resolution mass spectrometry).
9. General procedure for the synthesis of silacyclopentanes 4:
n-Butyllithium (0.14 mL, 1.6 M solution in hexanes,
0.225 mmol) was added to a solution of vinylsilane 1
(0.15 mmol) in dry diethyl ether (8 mL) at rt over 5 min.
The reaction mixture was stirred for 20 min and then
quenched with water (5 mL). The organic layer was
washed with water (8 mL) and dried over sodium sul-
phate. After removal of solvent in vacuo the residue was
purified by column chromatography on silica gel
(petroleum ether–dichloromethane, 20:1). Data for 4d:
obtained as a colourless oil (Z:E=19:1 by NMR spec-
troscopy), 81%, Rf 0.40 (petroleum ether–CH2Cl2, 10:1),
IR (neat): 3068, 2953, 1606, 1598, 1428, 1247, 1112, 837,
699 cm−1; lH (300 MHz, CDCl3) Z-isomer: 0.08 (9H, s,
Me3Si), 0.74 (3H, t, J=6.5 Hz, CH3), 0.85–1.54 (10H, m,
4×CH2 and CH2Si), 2.27 (1H, t, J=6.5 Hz, CH), 2.44–
2.57 (1H, m, CHaHbCꢁCH), 2.70–2.85 (1H, m,
CHaHbCꢁCH), 5.31 (1H, s, ꢁCHSi), 7.31–7.44 (6H, m,
Ph), 7.54–7.61 (4H, m, Ph); lC (75 MHz, CDCl3) Z-iso-
mer: 0.5, 9.5, 13.9, 22.3, 29.2, 31.9, 32.0, 33.4, 37.1, 121.9,
127.7, 127.8, 129.3, 129.5, 134.2, 134.9, 135.5, 136.3,
165.8; MS (EI): 392 (M+, 22%), 377 (7), 318 (8), 242 (65),
185 (65), 73 (100); HRMS (EI): 392.2354. Calcd for
C25H36Si2, 392.2356 (0.4 ppm error).
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