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21
Preparation of dithiocarbonic acid S
,
S
′-dibenzyl ester. To a 100 mL stainless steel autoclave, selenium (10 mmol), phenyl-methanethiol (20 mmol), and triethylamine (10 mmol) were added. The reactor was then sealed, flushed three times with carbon monoxide. Then carbon monoxide was introduced to the autoclave (0.8 MPa) and the reactor was placed in the oil bath preheated to 60 °C with stirring. After 10 h, the apparatus was cooled to room temperature and degassed. The pure dithiocarbonic acid S,S′-dibenzyl ester was obtained by column chromatography (silica gel, petroleum ether) in 96% yield. Recrystallization from ethanol gave colorless needles; mp 69-70 ° C (lit.
[22]
mp 45-46 °C); 1H NMR (400 MHz, CDCl3): δ = 7.31-7.21 (m, 10 H), 3.58 (s, 4 H).
24
Preparation of phenyl-thiocarbamic acid S-benzyl ester(2i) by the reaction of aniline with dithiocarbonic acid S
,
S
′-dibenzyl ester. To a 100 mL stainless steel autoclave, dithiocarbonic acid S,S′-dibenzyl ester (5 mmol), aniline (5 mmol) and chloroform (5 mL) were added. The reactor was then sealed and flushed three times with carbon monoxide. Then carbon monoxide was introduced to the autoclave (0.8 MPa, approximately 30-35 mmol), and the reactor was placed in the oil bath preheated to 60 °C with stirring. After 10 h, the apparatus was cooled to room temperature and degassed. The pure phenyl-thiocarbamic acid S-benzyl ester (2i) was obtained by column chromatography (silica gel, petroleum-chloroform, 1:1) in 86% yield. Recrystallization from chloroform-petroleum ether gave to colorless needles; mp 97-98 °C (lit.
[25]
mp 96-97 °C); 1H NMR (400 MHz, CDCl3): δ = 7.40-7.08 (m, 11 H), 4.22 (s, 2 H).
26
Typical experimental procedure is as follows (Table 1, entry 2): To a 100 mL stainless steel autoclave, selenium (0.5 mmol), nitrobenzene (10 mmol), propane-1-thiol (10 mmol), and triethylamine (5 mmol) were added. The reactor was then sealed, flushed three times with carbon monoxide. Then carbon monoxide was introduced to the autoclave (0.8 MPa, approximately 30-35 mmol), and the reactor was placed in the oil bath preheated to 60 °C with stirring. After 10 h, the apparatus was cooled to room temperature and degassed. The crude product was then dissolved in THF and stirred for 30 min to precipitate selenium. The catalyst was then recovered by filtration. The filtrate was concentrated. The pure phenyl-thiocarbamic acid S-propyl ester (2b) was obtained either by column chromatography (silica gel, chloroform-petroleum ether, 2:1) in 84% yield or by recrystallization from light petroleum ether in 72% yield as colorless needles; mp 83-84 °C (lit.
[27]
mp 84 °C); 1H NMR (400 MHz, CDCl3): δ = 7.42-7.07 (m, 6 H), 2.95 (t, J = 8.0 Hz, 2 H), 1.68 (sextet, J = 8.0 Hz, 2 H), 0.99 (t, J = 8.0 Hz, 3 H).
