ChemInform Abstract: Novel [1,N]-Carbon to Carbon Rearrangement of an Ester Group via Organotitanium Intermediates Wherein the N Varies from 2 to 5. Full Scope and Limitation Leading Predominantly to the Rearrangement.
✍ Scribed by T. YAMAZAKI; H. URABE; F. SATO
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 43 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Novel [1,N]-Carbon to Carbon Rearrangement of an Ester Group via Organotitanium Intermediates Wherein the N Varies from 2 to 5. Full Scope and Limitation Leading Predominantly to the Rearrangement.
-Olefinic or acetylenic di-or tricarboxylates are shown to undergo a novel type of carbon-to-carbon rearrangement of the ethoxycarbonyl groups mediated by a (η 2 -propene)Ti(O-iPr) 2 complex. Thus, the vinylmalonate (I) undergoes a 1,2-rearrangement, while for 1,3-, 1,4-, or 1,5-rearrangements the presence of an acetylene side chain is required. In the latter case, the rearrangements afford the corresponding olefins in E-geometry. Dealkynylation is observed to be a side process. -(YAMAZAKI, T.;