Interactions in Naphthalene Derivatives . An X - Ray Structure Determination and Nuclear Magnetic Resonance Studies of 1 , 8 - Di ( bromomethy 1 ) naphthalenel

Anal. Calcd for CzoHleOl: C, 75.0; H, 5.0. Found: C, 75.0; H, 5.0. 3-Deoxysericetin (16) and 3-Deoxyisosericetin (15). To a solution of 2 (500 mg) in dry benzene (40 ml) was added DDQ (300 mg) and the whole solution refluxed for 1 hr. It was filtered while hot, benzene distilled off, and the residue subjected to column chromatography. Elution with benzene-light petroleum (2%) gave a solid which again proved to be a mixture. Fractional crystallization with light petroleum (mother liquor A) yielded the sparingly soluble solid which on recrystallization from ethyl acetatelight petroleum mixture afforded 5-hydroxy-6-prenyl-6”,6”-dimethylpyrano[2”,3”:7,8]flavone [3-deoxyisosericetin (15)] (120 mg): mp 156”; Rf 0.78 (solvent A); light green ferric reaction; nmr 6 1.50 [s, 6, (CH&C<], 1.70, 1.83 [2 broad s, 6, (CH3)2C==], 3.41 (d, 2, J = 7 Hz, ArCHz), 5.33 (m, 1, -CH=), 5.67 6.88 (2 d, 2, J = 10 Hz, two olefinic H of pyran ring), 6.70 (s, 1 H in position 3), 7.59 (m, 3 H in positions 3’, 4’, and 5’) and 7.93 (m, 2 H in positions 2’ and 6’); mass spectrum (70 eV) m / e (re1 intensity) 388 (85), 373 (loo), 345 (57), 332 (63), 317 (l l) , 215 (17), 165 (ll), 105 (ll), 77 (10). Anal. Calcd for CzaH~404: C, 77.3; H, 6.2. Found: C, 76.8; H, 5.9. The mother liquor A yielded a solid which after crystallization twice from methanol yielded 5-hydroxy-8-prenyl-6”,6”-dimethylpyrano[2”,3”:7,6]flavone [3-deoxysericetin (IS)] (80 mg) as pale yellow needles: mp 166”; Rf 0.74 (solvent A); intense green ferric reaction; nmr 6 1.50 [e., 6, (CH&C<], 1.72, 1.79 [2d, 6, J = 2 Hz, (CH&C=], 3.56 (d, 2, J = 7 Hz, ArCHZ), 5.26 (m, 1, -CH=), 5.66, 6.81 (2 d, 2, J = 10 Hz, two olefinic H of pyran ring), 6.71 (s, 1 H in position 3), 7.59 (m, 3 H in positions 3’, 4‘, and 59, and 7.96 (m, 2 H in positions 2’ and 6’); mass spectrum (70 eV) m / e (re1 intensity) 388 (82), 373 (loo), 345 (68), 333 (73), 215 (28), 165 (14), 105 (27), 85 (36), 77 (22), 71 (55), 55 (46). Anal. Calcd for C25H2404: C, 77.3; H, 6.2. Found: C, 76.8; H, 5.9.