Tandem reverse-electron-demand diels-alder reactions of 1,5-cyclooctadiene.
✍ Scribed by J.Gabriel Garcia; Frank R. Fronczek; Mark L. McLaughlin
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 274 KB
- Volume
- 32
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Hexachlorocyclopentadiene and 5,5-dimethoxy-l,2,3.4-tetrachlorocyclopenta-2,4-diene react with 1,5-cyclooctadiene to produce a 1:4 syn to anti mixture of diadducts in good yield. The stereochemistry of the diastereomers is examined using X-my and molecular mechanics calculations are used to explore some of the potential causes for the observed diastereoselectivity.
📜 SIMILAR VOLUMES
The scope of 1,3,5-triazine inverse electron-demand Diels-Alder (IDA) reactions was expanded to include aminothiophenecarboxylic acids as latent dienophiles. A series of 2-amino-3-thiophenecarboxylic acids (1a-d) and a 3-amino-2-thiophenecarboxylic acid (5) were introduced as productive dienophiles
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Ultrasound irradiaton accelerates hetero Diels-Alder reactions between l-dimethylamino-I-azadienes and electron-defficient dienophiles. Besides the lower reaction times and increased yields, other advantages of the sonicated reactions are the possibility of isolating previously unknown adducts due t