Supplementary data
Determination of the electrophilic reactivities of 1,1,3-triarylallyl cations
Herbert Mayr,* Claudia Fichtner, and Armin R. Ofial
Department Chemie, Ludwig-Maximilians-Universit t München
Butenandtstr. 5-13 (Haus F), D-81377 München, Germany
UV-vis spectrum of the 1,1,3-triphenylallyl triflate (1a-OTf) in dichloromethane at -70 °C,
lmax = 515 nm; e = 1.18 × 105 L mol–1 cm–1.
UV-vis spectrum of the 1,1-bis(4-methoxy–phenyl)-3-phenylallyl triflate (1b-OTf) in dichloromethane at –70 °C,
lmax = 515 nm; e = 5.33 × 104 L mol–1 cm–1.
UV-vis spectrum of the 1,1-bis(4-dimethylaminophenyl)-3-phenylallyl tetra–fluoroborate (1c-BF4) in dichloromethane at +20 °C,
lmax = 661 nm; e = 5.95 × 104 L mol–1 cm–1.
UV-vis spectrum of the 1,1,3-tris(4-dimethylaminophenyl)allyl tetrafluoroborate (1d-BF4) in dichloromethane at +20°C,
lmax = 698 nm; e = 9.00 × 104 L mol–1 cm–1.
1,1,3-Triphenylhexa-1,5-diene (17)
Reaction of 1a-OTf with allylstannane 8
As described for the combination of 1a-OTf with 7, acetate 4a (0.65 g, 2.0 mmol), trimethylsilyl triflate (0.39 mL, 2.2 mmol) and allylstannane 8 (1.00 g, 2.56 mmol) reacted for 2 h. After work up and chromatography 17 (0.41 g, 66%) was isolated as a colourless oil which crystallised on standing, mp 56-57°C. The NMR spectra were identical to those of 17 obtained from the reaction of 1a-OTf with 7.
1,1-Bis(4-methoxyphenyl)-3-phenylhexa-1,5-diene (18)
As described for the formation of 19, compound 4b (0.21 g, 0.54 mmol), trimethylsilyl triflate (0.10 mL, 0.55 mmol), and allylstannane 9 (0.20 mL, 0.65 mmol) reacted for 3 d. After work up and chromatography 18 (0.08 g, 40%) was obtained as a yellow oil (Found C, 84.10; H, 7.12. C26H26O2 requires C, 84.29; H, 7.07%); dH (400 MHz, CDCl3)31 2.46–2.50 (2 H, m, 4-H2), 3.49–3.55 (1 H, m, 3-H), 3.77, 3.84 (2 × 3 H, 2 s, 2 × OMe), 4.93–5.02 (2 H, m, 6-H2), 5.61–5.72 (1 H, m, 5-H), 6.10 (1 H, d, J 10.5, 2-H), 6.76–6.79, 6.87–6.90, 7.02–7.05 (3 × 2 H, 3 m, ArH), 7.13–7.19 (5 H, m, ArH), 7.26–7.30 (2 H, m, ArH); dC (100 MHz, CDCl3)31 41.89 (t, C-4), 45.11 (d, C-3), 55.20, 55.27 (2 q, 2 × OMe), 113.42, 113.49 (2 d, ArH), 116.07 (t, C-6), 126.00, 127.40, 128.45, 128.46 (4 d, ArH), 130.45 (d, C-2), 130.96 (d, Ar), 132.60, 135.61 (2 s), 136.49 (d, C-5), 140.50, 145.08 (2 s), 158.59, 158.83 (2 s, Ar); m/z (EI) 370 (M+, 1%), 330 (26), 329 (100), 221 (18).

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