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Benzannulation and Cyclopentannulation Reactions of Electron-Poor Amino-Stabilized Alkenyl Fischer Carbene Complexes

✍ Scribed by José Barluenga; Luis A López; Silvia Martı́nez; Miguel Tomás


Book ID
104202637
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
162 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis


AbstractÐThe alkenyl(amino)carbene complexes of chromium and tungsten bearing an electron-withdrawing group at the C b -position 5±6 were prepared by condensation of methyl(amino)carbene complexes 1±2 and esters of glyoxylic acid. The complexes 5±6 were readily a-metallated with n-BuLi affording the deuteriated metal carbene complexes 7±8. The chromium complexes 5, 7 display a remarkable reactivity toward different types of alkynes. These complexes reacted with both unactivated alkynes and terminal electron-poor alkynes to give exclusively the phenol products 11±13 via the benzannulation reaction (Do Ètz reaction). In contrast, the reaction of carbene complexes 5 with internal electron-poor alkynes yielded solely the cyclopentadiene derivatives 15 via the cyclopentannulation reaction. The tetracarbonyl carbene intermediates 16 were isolated and fully characterized.


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ChemInform Abstract: Benzannulation and
✍ Jose Barluenga; Luis A. Lopez; Silvia Martinez; Miguel Tomas 📂 Article 📅 2000 🏛 John Wiley and Sons ⚖ 33 KB 👁 1 views

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