Synthetic route to benzo[c]thiophene and the naphtho[c]thiophenes

Abstract

to 200 ml of water containing 5.8 ml of acetic acid. After standing for 1 hr, the precipitate was collected and washed with cold water. The crude product (mp 319°, 62-74% yield) was crystallized from hot water (25-50% yield): mp 347°; ir (KBr) 3350 (broad), 3180 (broad), 2880 (broad), 1720, 1680,

Struktur und Reaktivität von isoanellierten heterocyclischen Systemen mit 4n;‐π‐ und (4n + 2)‐π‐Elektronen, XVIII. Benzo[c]thiophene mit symmetrischer Struktur: Modifizierte und optimierte Herstellung nach der S‐Oxid‐Route

“…15.00 g(5%)3bmit .3 g(61%)3b33i kristallisiert man sukzessiv aus ca. 1.6 1 Ligroin und 1.3 1 Essigester um; dabei muB die heil3e Losung von 3 b in Ligroin und Essigester filtriert werden, um das schwerer losliche 9,10-Dihydro-l, 2,3,4, 5,6,7,8- (19), 275 (32), 274 (17) (17), 271 (27) (28%) 1,2,3,4,8,9,fO,l f- 7,12,6] (14), 447 (16), 422 (23), 420 (36), 418 (24), 374 (14), 373 (28), 372 (32), 371 (29), 370 (30), 369 (13). 1430,1360,1335,1230,1195,1110,1020,995,830,730,710 1420, 1410, 1370, 1340, 1260, 1190, 1160, 1145, 1130, 880, 705. -'H-NMR (300 MHz, CDC13): 6 = 4.39 (s, 4H, CH2S).…”

Benzo[c]thiophene–C60 Diadduct: An Electron Acceptor for p–n Junction Organic Solar Cells Harvesting Visible to Near‐IR Light

“…Benzo[ c ]thiophene 4 was prepared according to a literature method:9a,b A mixture of 3 (800 mg, 5.26 mmol) and grade I neutral alumina (2.0 g) was heated for 2 h under 25 torr pressure at 130 °C in a sublimer to give 4 as a white solid (607 mg, 86 %). 1 H NMR (500 MHz, CDCl 3 ): δ =7.04 (dd, J =2.9, 6.9 Hz, 2 H; 5‐,6‐H), 7.60 (dd, J =2.9, 6.9 Hz, 2 H; 4‐,7‐H), 7.65 ppm (s, 2 H; 1‐,3‐H).…”

Recent trends in isomeric thienoquinoxalines [1980‐2000]

“…The ratio of exo/endo adducts varies a little due to reaction time and reaction temperature, but the formation of the exo isomer is generally favorable. The structures of 98a (exo) and 98b (endo) were assigned on the basis of their 1 H-nmr spectra by analogy with the corresponding N-phenyl adducts of benzo[c]thiophene [46,47] (Scheme 43).…”