Reaction of acylsilanes with potassium cyanide: Brook rearrangement under phase-transfer catalytic conditions
Tetrahedron letters Volume 41 Issue 21
Page 4169-4172
published_at 2000-05-29
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| File | |
| Title ( eng ) |
Reaction of acylsilanes with potassium cyanide: Brook rearrangement under phase-transfer catalytic conditions
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| Creator |
Ohnishi Yuji
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| Source Title |
Tetrahedron letters
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| Volume | 41 |
| Issue | 21 |
| Start Page | 4169 |
| End Page | 4172 |
| Abstract |
The reactions of acylsilanes with KCN under liquid–liquid phase-transfer catalytic conditions proceeded smoothly via the Brook rearrangement to produce O-silylated cyanohydrin derivatives in excellent yields. We also found that α-cyano carbanions generated by the Brook rearrangement in the reaction of (β-(trimethylsilyl)acryloyl)silane 7 can undergo alkylation at the γ-position and that in the reaction of β-bromoacylsilane 14 intramolecular alkylation occurs to afford cyclopropanone cyanohydrin derivative 16.
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| Keywords |
Cyanides
Cyanohydrins
Cyclization
Rearrangements
Silicon and Compounds
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| NDC |
Chemistry [ 430 ]
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| Language |
eng
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| Resource Type | journal article |
| Publisher |
Elsevier Science Ltd.
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| Date of Issued | 2000-05-29 |
| Rights |
Copyright (c) 2000 Elsevier Science Ltd.
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| Publish Type | Author’s Original |
| Access Rights | open access |
| Source Identifier |
[ISSN] 0040-4039
[DOI] http://dx.doi.org/10.1016/S0040-4039(00)00560-8
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