| 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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| Project Status |
Completed (Fiscal Year 1993)
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| Budget Amount *help |
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1993: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1992: ¥1,700,000 (Direct Cost: ¥1,700,000)
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| Keywords | ammonium ylide / sulfonium ylide / Sommelet-Hauser rearrangement / stevens rearrangement / [2,3] sigmatropic shift / ring enlargement / desilylation / fluoride ion / Sommelet-Hauser Rearrangement / Stevens Rearrangement / アンモニウムイリド / Sommelet-Hauser転位 / Stevens転位 / 環拡大反応 / 有機ケイ素化合物 / フッ素イオン / 中員環アミン |
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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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