Title of article :
Synthesis of arenediynes via the vinylidenecarbene–acetylene rearrangement
Author/Authors :
Sahu، نويسنده , , Bichismita and Namboothiri، نويسنده , , Irishi N.N. and Persky، نويسنده , , Rachel، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2005
Abstract :
A convenient method for the two-step synthesis of arenediynes from 1,2-arenedialdehydes is reported. Dibromomethylenation of dialdehydes under Corey–Fuchs conditions (CBr4, Ph3P, Zn) provides the tetrabromides in excellent yields. Treatment of the tetrabromides with n-BuLi or LDA affords 3,4-unsaturated 1,5-diynes, the key structural moiety present in several naturally occurring antitumour antibiotics, in varying yields. The key intermediates in these transformations appear to be vinylidenecarbenes or carbenoids, generated in situ via metal–halogen exchange and elimination.
Keywords :
Fritsch–Buttenberg–Wiechell rearrangement , Enediynes , Vinylidenecarbene
Journal title :
Tetrahedron Letters
Journal title :
Tetrahedron Letters