1-Hexene → HCID 15956438, compound

Participants

Reaction Steps

A solution containing 1-hexene (10 equiv.) and 1 mol % of rhodium (II) acetate in dry dichloromethane (10 mL) was degasified under an argon atmosphere. To this reaction mixture, a solution of 5-bromo-3-diazo-oxindole (1 equiv.) (J. Am. Chem. Soc. 1958, 80, 2257–2263) was added dropwise slowly over 1 h under an argon atmosphere at room temperature. The reaction mixture was stirred for 16 hours at room temperature, and concentrated to dryness in vacuo. The solid residue was chromatographed using hexane and ethyl acetate (v/v 1:1) as eluent. The chromatographed material gave the title compound in 70% yield. MS: m/z 294.3 [M+1]+. 1H NMR (CCl3D): δ 8.32 (br, 1H), 7.25 (d, 1H), 6.89 (d, 1H), 6.78 (d, 1H), 1.89 (m, 2H), 1.65 (m, 1H), 1.51 (m, 2H), 1.18–1.31 (m, 4H), 0.79 (t, 3H).

Provenance & Evidence