Compound 5
1-(2,6-diisopropylphenyl)-3,3,5,5-tetramethylpyrrolidine-2-selenone
From: Neutral zero-valent s-block complexes with strong multiple bonding
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
A suspension of 3 (37 mg, 0.06 mmol, 1.0 eq.) in C6D6 (0.8 mL) was treated with elemental selenium (10 mg, 0.12 mmol, 2.0 eq.) and stirred for 3 h at room temperature. A color change from purple to yellow was observed and the selenone [MeL=Se], 5 (Tretiakov, M. et al., Lewis-base stabilized diiodine adducts with N-heterocyclic chalcogenamides, Dalton Trans. 42, 12940–12946 (2013)), was identified by NMR spectroscopy as the only CAAC-containing product. 1H NMR (C6D6, 500 MHz): δ = 7.20 (t, JHH = 8 Hz, 1H, CHpara), 7.10 (d, JHH = 8 Hz, 2H, CHmeta), 2.83 (sept., JHH = 7 Hz, 2H, C H (CH3)2), 1.76 (s, 2H, CH2), 1.48 (s, 6H, CH3), 1.46 (d, JHH = 7 Hz, 6H, CH(C H3)2), 1.19 (d, JHH = 7 Hz, 6H, CH(C H3)2), 0.96 (s, 6H, CH3). 13C{1H} NMR (C6D6, 125 MHz): δ = 219.4 (Cq,carbene), 147.2 (Cq), 134.8 (Cq), 29.2 (CHpara), 125.0 (CHmeta), 71.5 (Cq), 53.5 (Cq), 50.8 (CH2), 32.2 (CH3), 29.7 (C H(CH3)2), 28.6 (CH3), 27.3 (CH( C H3)2), 23.7 (CH( C H3)2). 77Se (C6D6, 95 MHz): 492.4 ppm.
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313189033
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