Synthesis of distyryl derivatives of five‐membered heterocycles

Aromatic substitution of olefins. XXV. Reactivity of benzene, naphthalene, ferrocene, and furan toward styrene, and the substituent effect on the reaction of monosubstituted benzenes with styrene

“…Styryl-Substituted Aromatic Compounds, irons-2-Styrylnaphthalene (2), mp 143 °C,22 irons-styrylferrocene (4), mp 119-119.5 °C,23 irons-2-styrylfuran (5), mp 52.5-54 °C,24 trans,trans-2,5distyrylfuran (6), mp 144-145.5 °C. 24 General Procedure for Reaction of Monosubstituted Benzenes with Styrene. Mixtures of palladium acetate (6 mmol), styrene (6 mmol), monosubstituted benzene (60 ml), and acetic acid (14 ml) were stirred for 8 h at 110 °C.…”

Condensations of thiophene with ketones

“…Calc. for C 12 H 14 S 2 : M, 222.0537); m/z 222 (8%, M ϩ ), 193 (100, M Ϫ Et), 109 (14, C 6 H 5 S) and 83 (78, C 4 H 3 S); λ max /nm 232infl (3.88); ν max /cm Ϫ1 1589 (aromatic C᎐ ᎐ C); δ H 0.86 (3H, t, J 8, CH 2 CH 3 ), 1.76 (3H, s, CH 3 ), 2.19 (2H, q, J 8, CH 2 Me),6.82 (2H, d, J 3, H-3),6.88 (2H, dd, J 3 and 5, H-4), and 7.12 (2H, d, J 5, H-5).Next came 2,5-bis[2-(2-thienyl)butan-2-yl]thiophene 2 (890 mg, 2.5 mmol, 9.9%) (Found: M ϩ , 360.1053. C 20 H 24 S 3 requires M, 360.1040); m/z 360 (19%, M ϩ ), 331 (100, M Ϫ Et), 302 (47, 331 Ϫ Et), 287 (5, 302 Ϫ Me), 218 (9, C 12 H 10 S 2 ), 109 (27, C 6 H 5 S), and 97 (15, C 5 H 5 S); λ max /nm 235 (log ε 4.26); δ Et) ϩ , 607.1655.…”