2001 Fiscal Year Final Research Report Summary
Development of Novel method for Synthesizing Macrocyclic Compounds Utilizing Characteristic Bonding properties of Hypervalent Sulfur
| Project/Area Number |
12640525
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
Organic chemistry
|
|---|
| Research Institution | Osaka Prefecture University |
|---|
Principal Investigator |
MATSUMURA Noboru Osaka Prefecture University, Graduate School, Lecturer, 大学院・工学研究科, 講師 (40125274)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
MIZUNO Kazuhiko Osaka Prefecture University, Graduate School, Professor, 大学院・工学研究科, 教授 (10109879)
|
|---|
| Project Period (FY) |
2000 – 2001
|
| Keywords | Hypervalent Sulfur / Tetraazathiapentalene / Macrocycles / Ring-Opening / Recognition / Neutral Anion Receptor |
|---|
| 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.
|
