Development of a new Synthetic Method of Thiol Esters by Using Carbon Monoxide-Disulfide System
| Project/Area Number |
12650840
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
有機工業化学
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| Research Institution | Kansai University |
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Principal Investigator |
SONODA Noboru Kansai University, Faculty of Engineering, Professor, 工学部, 教授 (20083983)
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| Co-Investigator(Kenkyū-buntansha) |
NISHIYAMA Yutaka Kansai University, Faculty of Engineering, Associate Professor, 工学部, 助教授 (30180665)
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| Project Period (FY) |
2000 – 2001
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| Project Status |
Completed (Fiscal Year 2001)
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| Budget Amount *help |
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2001: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2000: ¥2,200,000 (Direct Cost: ¥2,200,000)
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| Keywords | Selenium / Carbon Monoxide / hrolester / Disulfide / セレン触媒 |
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| Research Abstract |
The development of a convenient and efficient method for the synthesis of S-alkyl and S-arylcarbonothiolates has attracted considerable attention in synthetic and industrial chemistry. Hitherto, although many synthetic methods of S-alkyl- and S-arylcarbonothiolates have been shown, these methods consisted on a multi-step procedures: (i) the preparation of SCO by the reaction of sulfur with carbon monoxide, (ii) the nucleophilic addition of alcohol or thiol and (iii) subsequent alkylation.
Now we found a one-pot synthetic method of S-alkyl- and S-arylcarbonothiolates by the reaition of alcohol with disulfide and carbon monoxide in the presence of a catalytic amount of selenium. For example, when ethanol was treated with diphenyl disulfide in the presence of a catalytic amount of selenium under an atmosphere pressurized of carbon monoxide, S-phenyl-O-ethylcarboncpthiolate was formed in almost quantitative yield. Similarly, diaryl disulfide substituted various functional groups were reacted with ethanol under the pressure of carbon monoxide to give the corresponding S-aryl-O-ethylcarbonothiolates in moderate to good yields. In this reaction, aliphatic alcohols can also be used as an alcohol, the corresponding thiol esters were formed in moderate yields. On the other hand, in the case of dialkyl disulfide, the mixture of S- alkyl- O- alkylcarbonothiolates and S, S- dialkylcarbonothiolates were obtained.
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Report
(3 results)
Research Products
(9 results)
