Reactivity of 4,6-dioxy-2-pyrones in the Diels-Alder process
β Scribed by Alan P. Kozikowski; Richard Schmiesing
- Publisher
- Elsevier Science
- Year
- 1978
- Tongue
- French
- Weight
- 220 KB
- Volume
- 19
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
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Ab5tract: 4-Ethyl-5-methyl-6-mthylthio-2(H)-pyranone (4) undergoes Dials-Alder reactions with ethyl hexynoate (5). 3-heptyn-2-one (6). ethyl ptopiolate (7). and3-butyn-2-one (8) to afford substituted banzenes with high ragioselectivity upon extrusion of CO2. 4-Ethyl-5.6-dimethyl-( 4-ethyl-3,6-dimeth
## Abstract Under basic conditions 2,6βbis(bromomethyl)β4βpyrone **8** reacts with tetraethylene glycol to yield the unexpected macrocycle **9**, which is related to the antibiotic Kjellmanianone **10**. We propose that this ring transformation proceeds __via__ the cyclopropyl intermediate **d** (S
The reactivity of 2-alkylidene-imidazolidines 2 in inverse Diels-Alder syntheses with several pyridazines and 1,2,4-triazines is compared with that of acyclic ketene acetals 1. The 2-cyclopropylidene-imidazolidine 2~ is particularly suited for less reactive dienes. Extensive work of Sauer 1) and ot