✦ LIBER ✦
ChemInform Abstract: Base-Induced Cyclization of 1-Benzyloxy-2,2,4,4-tetramethylpentan-3-ones: Intramolecular Nucleophilic Addition of an Anion of a Benzyl Ether to the Carbonyl Moiety Without the Wittig Rearrangement or Protophilic Decomposition.
✍ Scribed by M. MATSUMOTO; N. WATANABE; A. ISHIKAWA; H. MURAKAMI
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 35 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Base-Induced Cyclization of 1-Benzyloxy-2,2,4,4-tetramethylpentan-3-ones: Intramolecular Nucleophilic Addition of an Anion of a Benzyl Ether to the Carbonyl Moiety Without the Wittig Rearrangement or Protophilic Decomposition.
-Two combinations of base and solvent are found to be effective for the title reaction of ethers like (I). Their influence on the cis-or trans-configuration of the obtained products is discussed. Both isomeric tetrahydrofurans (IIa) and (IIIa) are easily dehydrated to give compound (IV), a key intermediate for the dioxetane synthesis, in high yield.