Synthesis of 9-Alkyl- and 9-Arylthiophenanthrenes

Electrochemical Activation of Dimethyl Disulfide for Electrophilic Aromatic Substitution

“…In addition, the structure of ( 7) SbCl 6 was unequivocally established by X-ray crystallographic analysis. Treatment of 6 with sodium methoxide in anhydrous methanol produced 9-methylthiophenanthrene, 9 , in 61% isolated yield. Reaction of 7 with DBU formed 10 in 76% isolated yield.…”

“…The mixture was extracted with CH 2 Cl 2 (3 × 10 mL), and the combined extracts washed with 5% aqueous HCl solution and then brine. The organic phase was separated, dried (anhyd MgSO 4 ), filtered, concentrated by rotary evaporation, and chromatographed on silica gel (eluting with CH 2 Cl 2 /pentane) to give pure 9 (14 mg, 61% yield) …”

Two 9-alkylthiophenanthrenes at 193 K (alkyl = dodecyl and tetradecyl)

“…The 9-alkylthiophenanthrenes were prepared from 9-bromophenanthrene, KOH and alkylthiol in dimethylformamide according to a previously reported procedure (Sipila È & Hase, 1997). The side product dialkyl disul®de was removed by¯ash chromatography and the crystals suitable for X-ray analysis were obtained by recrystallization from ethanol.…”

Crystallographic and NMR analysis of 9-phenylthiophenanthrene and 9-tert-butylthiophenanthrene

“…In connection with earlier studies on the preparation and reactions of new hemithiodithioacetals we developed an easy and reliable synthesis of 9-alkyl-and 9-arylthiophenanthrenes. 1 The present article reports X-ray and NMR structural studies on 9-phenylthiophenanthrene C 20 H 14 S (1) and 9-tert-butylthiophenanthrene C 18 H 18 S (2). We have earlier reported crystal structures of straight-chained 9-alkylthiophenanthrenes [alkyl = methyl, C 15 H 12 S (3a, 3b), ethyl C 16 H 14 S (4), propyl C 17 H 16 S (5), and butyl C 18 H 18 S (6)].…”