1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane → Allyl-dimethyl-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)stannane

Beteiligte Stoffe

Reaktionsschritte

Freshly prepared allyldimethyltin chloride (2.86 g, 12.7 mmol) was added dropwise to the Grignard reagent of C6F13CH2CH2MgI, which was prepared from C6F13CH2CH2I (6.0 g, 12.7 mmol) and magnesium powder (0.37 g, 15.2 mmol). The reaction mixture was refluxed overnight (16 h) before quenching with 1N HCl. The crude product was purified by vacuum distillation (112° C./water pump) to give pure 2a as a colorless oil (3.20 g, 35%). 1H NMR (CDCl3) δ 5.95-5.86 (m, 1H), 4.85-4.80 (dd, J=16.8, 1.4 Hz, 1H), 4.73-4.69 (dd, J=11.8, 1.8 Hz, 1H), 2.30-2.12 (m, 2H), 1.83 (d, J=8.5 Hz, 2H), 1.00-0.92 (m, 2H), 0.15 (s, JSn-H=26.3 Hz, 6H); 13C NMR (CDCl3) δ 136.8, 121.8-107.2 (m), 27.9 (t), 16.9, −1.8, −12.2; 19F NMR (CDCl3) δ −81.3 (3F), −117.2 (2F), −122.5 (2F), −123.4 (2F), −123.9 (2F), −126.7 (2F); 119Sn NMR (C6D6): δ −1.4; HRMS: calc. 496.9597 (M+-Me), found: 496.9583. IR (thin film): 1626 cm−1.

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