Title of article :
A selective synthesis of 2-([2,2]paracyclophan-5-yl)pyrrole from 5-acetyl[2,2]paracyclophane via the Trofimov reaction
Author/Authors :
Schmidt، نويسنده , , Elena Yu and Zorina، نويسنده , , Nadezhda V and Zaitsev، نويسنده , , Alexey B and Mikhaleva، نويسنده , , Alʹbina I and Vasilʹtsov، نويسنده , , Alexander M and Audebert، نويسنده , , Pierre and Clavier، نويسنده , , Gilles and Méallet-Renault، نويسنده , , Rachel and Pansu، نويسنده , , Robert B، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2004
Abstract :
Rearrangement of 5-(1-vinyloxyiminoethyl)[2,2]paracyclophane, the key intermediate of the Trofimov reaction (pyrrole formation from ketoximes and acetylene), gives (120 °C, 30 min, DMSO) 2-([2,2]paracyclophan-5-yl)pyrrole in 74% yield. The intermediate 5-(1-vinyloxyiminoethyl)[2,2]paracyclophane has been synthesised in 78% yield by vinylation of the Cs-derivative of the oxime of 5-acetyl[2,2]paracyclophane with acetylene under pressure in the DMSO–n-pentane two-phase system (70 °C, 5 min).
Keywords :
O-Vinyloxime , 2]Paracyclophan-5-yl)pyrrole , 2-(2 , pyrrole , 2]paracyclophane , Oxime , Acetylene
Journal title :
Tetrahedron Letters
Journal title :
Tetrahedron Letters
