Development of Novel method for Synthesizing Macrocyclic Compounds Utilizing Characteristic Bonding properties of Hypervalent Sulfur
| Project/Area Number |
12640525
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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 |
Organic chemistry
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| Research Institution | Osaka Prefecture University |
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Principal Investigator |
MATSUMURA Noboru Osaka Prefecture University, Graduate School, Lecturer, 大学院・工学研究科, 講師 (40125274)
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| Co-Investigator(Kenkyū-buntansha) |
MIZUNO Kazuhiko Osaka Prefecture University, Graduate School, Professor, 大学院・工学研究科, 教授 (10109879)
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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 |
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2001: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2000: ¥2,100,000 (Direct Cost: ¥2,100,000)
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| Keywords | Hypervalent Sulfur / Tetraazathiapentalene / Macrocycles / Ring-Opening / Recognition / Neutral Anion Receptor |
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| Research Abstract |
In this report, we describes the novel method for synthesizing macrocyclic compounds utilizing characteristic bonding properties of hypervalent sulfur. Treatment of 2, 3 - dimethyltetraazathiapentalene derivative (1) with 1 equiv. of diisothiocyanate derivatives in refluxing benzene for 24h gives the macrocyclic compounds (2) with two tetraazathiapentalene skeletons in good yield. The reaction of (2) with NaBH_4 in DMSO at room temperature for 24h affords the ring-opened macrocyclic compound (3) that contains four thiourea moieties in this rings. The structure of (3) with p-xylylene unit is confirmed by X-ray crystallographic analysis. The treatment of (2) with an aqueous EtOH-KOH solution gives the ring-opened macrocyclic compound (4) having four thiourea moieties in the ring by the elimination of the C=S^<IV>moiety. The macrocyclic compounds (3) and (4) having p-xylylene unit serves as anion receptor for CH_3COO^- and H_2PO_4^- ions. The macrocycles having trans-azobenzene unit as spacer capture efficiently only CH_3COO^-. However, the cis isomer which produced by the light irradiation does not serve as anion receptor.
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Report
(3 results)
Research Products
(4 results)
