Synthesis of Dibenzo[d,g][1,3,6]trithiocins

Abstract

6-Acetoxy-, 6-methoxy-, 6-azido-, and 6-(methylthio)dibenzo[d,g][1,3,6]trithiocins (13, 14, 17, and 18, respectively) were synthesized by reactions of 9aH-9,10-dithia-4b-thioniaindeno[1,2-a]indene chloride (4) with appropriate nucleophiles in good yields. The trithiocin 13 was also prepared by the Pummerer reaction of dibenzo[d,g][1,3,6]trithiocin 5-oxide (12) in 97% yield. In many reactions of 4 with nucleophiles, the trimeric partial hydrolysis product, bis{o-[(dibenzo[d,g][1,3,6]trithiocin-6-yl)thio]phenyl} sulfide (15), was formed either as the major or a minor product. Structure of 15 was determined by X-ray diffraction analysis. Meanwhile, heating 4 in boiling methanol or ethanol gave the hydrolysis product, bis(o-mercaptophenyl) sulfide (16), in good yields. Condensation of 16 with benzaldehyde and pivalaldehyde gave 6-phenyl- and 6-t-butyldibenzo[d,g][1,3,6]trithiocins in good yields.

Synthesis and structural characterization of sulfur rich iron (II) carbonyl dimers: Facile reversible reaction with carbon monoxide

“…Fe 2 (CO) 9 (Strem), isopentyl nitrite (Aldrich), anthranilic acid (Aldrich), ethylene trithiocarbonate (Aldrich) and propylene oxide (Aldrich), were used as received. S 0 (SH) 2 and S 0 ( Si SH) 2 were prepared using slight modification of the literature procedures, as detailed below [11,[16][17][18]. [Fe(CO) 2 (S 0 S 2 )] 2 was prepared by reaction of [Fe(CO) 3 (PhCH@CHCOMe)] [22] with S 0 SH 2 .…”

“…A more convenient synthesis of S 0 (SH) 2 was developed by Nakayama and coworkers, who have used this compound in the synthesis of thioether crowns [16][17][18]. This synthesis is based on the dipolar cycloaddition reaction of ethylene trithiocarbonate with two equivalents of benzyne.…”