1990 Fiscal Year Final Research Report Summary
Direct Conversion Reaction of Toluenes to Conjugated-Trienes and Their Applications
| Project/Area Number |
01571160
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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 Pharmaceutical Sciences Professor, 薬学部, 教授
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| Project Period (FY) |
1989 – 1990
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| Keywords | Ylide / Ammonium Salt / Sigmatropic Rearrangement / Sommelet-Hauser Rearrangement / Stevens Rearrangement / Conjugated-Triene / Organosilicon Compound / Amine |
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| Research Abstract |
When trialkylbenzylammonium salts were treated with a strong base such as sodium amide in liquid ammonia, benzylammonium N-ylides intermediates are initially formed which subsequently rearrange to 6-aminomethyl-5-methylene-1,3-cyclohexadenes (conjugated trienes) via a [2,3] sigmatropic pathway. However, isolation of the trienes was difficult because they were quickly aromatized to 2-methylbenzylamines (Sommelet-Hauser rearrangement).
N-Methylide formation reaction in non-basic mediums was revealed as a result of fluoride-ion induced desilylation reaction of N- (trimethylsilyl) methylammonium salts with cesium fluoride in dimethylformamide or hexamethylphosphoramide at room temperature in our laboratory. In this reaction condition, some conjugated triene compounds which were rearrangement products of benzylammonium N-methylides, were stable enough to isolate at room temperature and applied for DielsーAlder reaction to give polycyclic amines.
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