Compound 6
(1-(2,6-diisopropylphenyl)-3,3,5,5-tetramethylpyrrolidine-2-ylidene) carbon dioxide adduct
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.
Reactivity of 3 with CO2: A J. Young ampoule was charged with a solution of 3 (50 mg, 0.09 mmol, 1.0 eq.) in THF (4 mL) and placed under an atmosphere of CO2. At room temperature, a color change from purple to light yellow was observed and a black precipitate was formed. [(MeL)CO2], 6 (Pratap Singh, A. et al., A singlet biradicaolid Zinc Compound and Its Nonradical Counterpart, J. Am. Chem. Soc. 135, 7324–7329 (2013)), was identified by NMR spectroscopy as the only CAAC-containing product. 1H NMR (THF-d8, 500 MHz): δ = 7.38 (t, JHH = 8 Hz, 1H, CHpara), 7.28 (d, JHH = 8 Hz, 2H, CHpara), 2.82 (sept., JHH = 7 Hz, 2H, C H (CH3)2), 2.28 (s, 2H, CH2), 1.60 (s, 6H, CH3), 1.45 (s, 6H, CH3), 1.35 (d, JHH = 7 Hz, 6H, CH(C H3)2), 1.29 (d, JHH = 7 Hz, 6H, CH(C H3)2). 13C{1H} NMR (THF-d8, 125 MHz): δ = 195.0 (Cq), 157.5 (Cq), 147.0 (Cq), 130.8 (CHpara), 130.4 (Cq), 125.9 (CHmeta), 79.4 (Cq), 50.2 (CH2), 48.0 (Cq), 30.3 (C H(CH3)2), 29.1 (CH3), 28.8 (CH3), 26.7 (CH( C H3)2), 24.5 (CH( C H3)2).
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313189034
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