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First [2 + 2]-Cycloaddition of a 3,4-Didehydropyridine and a Ketene Dialkyl Acetal.

✍ Scribed by Natacha Mariet; Malika Ibrahim-Ouali; Maurice Santelli

Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
33
Category
Article
ISSN
0931-7597

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First [2+2]-cycloaddition of a 3,4-dideh
First [2+2]-cycloaddition of a 3,4-didehydropyridine and a ketene dialkyl acetal
✍ Natacha Mariet; Malika Ibrahim-Ouali; Maurice Santelli πŸ“‚ Article πŸ“… 2002 πŸ› Elsevier Science 🌐 French βš– 62 KB

The 3-or 4-halopyridines and a ketene dialkyl acetal were shown to permit the synthesis of pyrido[b]cyclobutene derivatives. This finding constitutes the first published report of cycloadditions involving an olefin and a 3,4-pyridyne partner. The reaction is totally regioselective and the structure

ZnCl2-catalysed cycloadditions between k
ZnCl2-catalysed cycloadditions between ketene acetals and Ξ±,Ξ²-unsaturated carbonyl compounds. A simple route to 2,2-dialkoxy-3,4-dihydropyrans
✍ C. G. Bakker; J. W. Scheeren; R. J. F. Nivard πŸ“‚ Article πŸ“… 2010 πŸ› Elsevier Science 🌐 English βš– 665 KB

## Abstract 2,2‐Dialkoxy‐3,4‐dihydropyrans (3) can be obtained under mild conditions and in good yields from ketene acetals (1) and Ξ±,β‐unsaturated carbonyl compounds (**2**) in the presence of ZnCl~2~. At low temperatures (< βˆ’20Β°C) the reaction between **1** and **2** proceeds as a (2 + 2)‐cycload