Compound 4n
2'H-spiro[bicyclo[4.2.0]octa-1,3,5-triene-7,1'-naphtho[2,1-b]furan]
From: Remote C−H alkylation and C−C bond cleavage enabled by an in situ generated palladacycle
View in PubChem | 1H NMR | 13C NMR | MDL Molfile | ChemDraw
Compound data: CIF
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Prepared according to the general procedure outlined in the synthesis of 4a. 4n (58.5 mg, 75%) was obtained as a white solid, m.p. 95-97 oC (hexane); 1H NMR (400 MHz, CDCl3) δ = 7.80-7.73 (m, 1 H, Ar-H), 7.69 (d, J = 8.8 Hz, 1 H, Ar-H), 7.40-7.34 (m, 1 H, Ar-H), 7.32-7.23 (m, 2 H, Ar-H), 7.23-7.08 (m, 4 H, Ar-H), 7.08-7.03 (m, 1 H, Ar-H), 4.96 (d, J = 9.6 Hz, 1 H, one proton from OCH2C), 4.89 (d, J = 9.6 Hz, 1 H, one proton from OCH2C), 3.88 (d, J = 14.0 Hz, 1 H, one proton from CH2C), 3.56 (d, J = 14.0 Hz, 1 H, one proton from CH2C); 13C NMR (100 MHz, CDCl3) δ = 158.3, 148.8, 143.1, 130.5, 130.3, 129.8, 129.0, 128.7, 128.0, 126.8, 123.5, 122.8, 121.8, 121.3, 120.5, 112.3, 81.3, 57.4, 46.7; IR (CHCl3, cm-1) 3065, 2920, 1626, 1595, 1522, 1456, 1373, 1256, 1207; HRMS (DART) calculated for C19H15O [M+H+]: 259.11229, found: 259.11176.
