9-Vinylanthracene

yellow to green crystalline solid

(b) Grignard reaction: A solution of anthrone (15.0 g, 0.08mol) dissolved in dry THF (200 mL), was added to a mixture ofvinylmagnesium bromide (11.80 g, 0.09 mol) in dry THF (80 mL), maintained at 55 oC. The mixture was refluxed for 4h, cooledand then hydrolysed with 4N HCl (50mL). The organic layer wasextracted with benzene (70 mL). The extract was washed with waterand dried with anhydrous Na2SO4. The filtrate was added at roomtemperature to P2O5 (10 g) in anhydrous benzene (250 mL) withstirring over a 40 h period. Subsequently the filtrate was evaporatedto dryness, giving a crude solid, which was purified by columnchromatography over silica gel using hexane as eluent to give 6a inpure form. Yield 70percent; m.p. 65 °C; IR vmax (KBr) 3075 cm-1 (=CH2), 3043 cm-1 (=CH), 1625 cm-1 (C=C); UV lmax (CH3CN) 250 (e73, 000), 330 (e 2, 500), 385 (e 4, 900); 1H NMR (CDCI3) d 5.66 (1H, dd, Jtrans = 17.7 Hz, Jgem = 2.1 Hz, vinylic), 6.04 (1H, dd, Jtrans = 11.4Hz, Jgem = 2.1 Hz, vinylic), 7.46-8.40 (l0H, m, aromatic and vinylic).Anal. calcd for C16H12:C, 94.08; H, 5.92; found: C, 94.3l; H, 5.72percent.General procedure: General procedure C: preparation of compounds A17-A24 via catalytic Wittig reaction.In air, a 1-dram vial equipped with a stir-bar was charged with Aid (0.2 mmol, 20 molpercent) and A2 (2.0-3.5 mmol, 2.0-3.5 equiv.). If solid, aldehyde (1.0-1.2 mmol, 1.0-1.2 equiv.) was also added at this point. The vial was then sealed with a septum and purged with argon. Toluene (1.4 mL) and liquid reagents were introduced in the following quantities: aldehyde (1 .2 mmol, 1 .2 equiv.) and organohalide (1 .0 mmol, 1 .0equiv.). Diphenylsilane (1.2 mmol, 1.2 equiv.) was introduced and the septum was replaced with a PTFE-lined screw cap under an inert atmosphere. The reaction was heated at 140 00 or 150 00 for 24-48 h. Additional portions of base and halide were added at 24 h for 48 h reactions. The crude reaction mixture was filtered through Celite®, concentrated in vacuo, and purified via flash column chromatography. . 9-Ethenylanthracene (A23) was obtained from the reaction of 9-anthracenecarboxaldehyde (128 mg, 0.6 mmol, 1.2 equiv.), methyliodide (31 pL, 0.5 mmol, 1.0 equiv.), diphenylsilane (112 pL, 0.6 mmol, 1.2 equiv.) andA2 (210 mg, 1.5 mmol, 3.0 equiv.) using A3b (30 mg, 20 mol percent) in toluene (0.7 mL) at140 00 for 24 h. Methyl iodide and A2 were added in two portions, at 0 h and 4 h. Thecrude product was purified via flash column chromatography (hexane, R = 0.35) toafford A23 as a yellow liquid (66 mg, 65percent). 1H NMR (400 MHz, ODd3) 6: 5.68 (d, J =18.0 Hz, 1 H), 6.06 (d, J = 11.5 Hz, 1 H), 7.48-7.60 (m, 5H), 8.00-8.08 (m, 2H), 8.35-8.40 (m, 2H).

Molecular Weight:204.27
XLogP3:5.5
Rotatable Bond Count:1
Exact Mass:204.093900383
Monoisotopic Mass:204.093900383
Heavy Atom Count:16
Complexity:233
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes