1993 Fiscal Year Final Research Report Summary
New Development of the Chemistry of N-Ylides and S-Ylides
| Project/Area Number |
04671301
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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 Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (80080183)
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| Co-Investigator(Kenkyū-buntansha) |
SHIRAI Naohiro Faculty of Pharmaceutical Sciences, Lecturer (80080208)
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| Project Period (FY) |
1992 – 1993
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| Keywords | ammonium ylide / sulfonium ylide / Sommelet-Hauser rearrangement / stevens rearrangement / [2,3] sigmatropic shift / ring enlargement / desilylation / fluoride ion |
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| Research Abstract |
Fluoride ion induced desilylation of alpha-trimethylsilyl-substituted ammonium (1, Y=NMe) and sulfonium salts (1, Y=S) gave the corresponding ammonium and sulfonium ylides (2) in quantitative yields.
Cyclic ammonium ylides (2, Y=NMe) converted to [2,3] sigmatropic rearrangement products (3) and/or Stevens products (4). Telation of their rations with the stereoisomers of 1 was investigated.
Selection of the formation path of 3 or 4 was achieved when the reaction of 1 (Y=NMe) was carried out under UV irradiation or in the presence of DBU.
sulfonium ylides (2, Y=S) gave selectively Sommelet-Hauser products.
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[Publications] Yoshiro Sato^*, Naohiro Shirai, Yoshio Machida, Emiko Ito, Takayo Yasui, Yukihisa Kurono, and Keiichiro Hatano: "Rearrangements of 1,6,7-Trisubstituted 2-methyl-1,2,3,4-tetrahydroisoquinolinium 2-Methylides" J.Org. Chem. 57. 6711-6716 (1992)
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