1989 Fiscal Year Final Research Report Summary
Organic Syntheses Utilizing Trimethylsilyldiazomethane
| Project/Area Number |
63571001
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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 |
AOYAMA Toyohiko Nagoya City University, Faculty of Pharmaceutical Sciences, Lecturer, 薬学部, 講師 (80080191)
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| Project Period (FY) |
1988 – 1989
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| Keywords | trimethylsilyldiazomethane / lithium trimethylsilyldiazomethane / alpha-trimethylsilyldiazoalkane / (E)-vinylsilane / (Z)-vinylsilane / 1, 2, 3-triazole / olefin / quinone |
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| Research Abstract |
Synthetic utilizations of trimethylsilyldiazomethane (TMSCHN_2), as a stable and safe substitute for hazardous diazomethane, were investigated as follows: 1. The cuprous chloride-catalyzed decomposition of alpha-trimethylsilyldiazoalkanes gives (E)-1-trimethylsilyl-1-alkenes in high yields. 2. Lithium trimethylsilyldiazomethane smoothly reacts with ketenimines to give 1,2,3-triazoles in good yields. 3. Most of the reactions of TMSCHN_2 with various olefins in the presence or absence of metal salt catalysts give silylcyclopropanes. 4. The rhodium(II) pivalate-catalyzed decomposition of alpha-trimethylsilyldiazoalkanes stereoselectively affords (Z)-1-trimethylsilyl-1-alkenes,in,good yields. 5. Reaction of TMSCHN_2 with various quinones affords indazoles, silylcyclopropanes, 2-substituted 3-trimethylsilylmethylml,4-quinones, and trimethylsilylmethylenedioxy derivatives,depending upon substrates.
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