Reactions of trifluoromethylcyclopentadiene, 2-propyn-1-ol, and base

✍ Scribed by Thomas Olsson; Olof Wennerström

• Book ID: 104244750
• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 232 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93635-4

✦ Synopsis

TrifZuoromethylcycZopentadiene, 2propyn-l-01, and base can give either propynyL 5-allenyt cyctopentaclienecarboxytate, 1 , or tri(2-propynyll cyclopentadieneorthocarboxylate, 2. The latter undergoes an intramolecular Die&-Alder reaction to the norbormdiene derivative 3a.

Claisen rearrangements of ally1 vinyl ethers and ally1 aryl ethers are important tools for the synthesis of natural products and other complex compounds.

1 The reaction is concerted and classified as a [3,3] sigmatropic reaction. 2 The Claisen rearrangement of aryl ally1 ethers usually requires