| Project/Area Number |
06672105
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Nagoya City University |
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Principal Investigator |
SATO Yoshiro Nagoya City University, Faculty of pharmaceutical Sciences, Professor, 薬学部, 教授 (80080183)
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| Project Period (FY) |
1994 – 1995
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| Project Status |
Completed (Fiscal Year 1995)
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| Budget Amount *help |
¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1995: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1994: ¥1,200,000 (Direct Cost: ¥1,200,000)
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| Keywords | N-Ylide / S-Ylide / Ring-Enlargement / Sommelet-Hauser Rearrangement / Stevens Rearrangement / Cyclic Sulfide / Cyclic Amine / Organosilicon Compound / 寛恕スルフィド / アンモニウムイリド / スルホニウムイリド / [2,3]シグマトロピー転位 / 脱シリル化 / フッ素イオン |
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| Research Abstract |
Reaction of tetraalkylammonium or trialkylsulfonium salts, which are substituted at an alpha-position with a trimethylsilyl group, with cesium fluoride in an aprotic solvent gave the correspond-ing N-ylide or S-ylide intermediates in quantitative yields at room temperature. Because these ylides are formed under non-basic conditions, their rearrangement might be applicable for various ammonium and sulfonium compound having functional groups. Thus the following reactions were examined.
1. N-Ylides
(1) Relation between stereochemistry of 5-or 6-membered cyclic ammonium methylides and their rearrangements was investigated.
(2) The effect of substituents and configuration of the isotoluene derivatives which were produced by a [2,3] sigmatropic migration of benzylammonium metheylides was investigated.
(3) Sommelet-Hauser rearrangement to pyridine, pyrrole and indole rings was investigated.
2. S-Ylides
(1) Chemical behavior of benzylsulfonium S-methylides was investigated.
(2) Rearrangement of six-membered cyclic sulfonium S-methylides was investigafed.
(3) Usefulness of diphenylsulfonium S-methylide in non-basic media for organic synthesse was investigated
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