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Synthesis of arenediynes via the vinylidenecarbene-acetylene rearrangement

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Title Synthesis of arenediynes via the vinylidenecarbene-acetylene rearrangement
 
Creator SAHU, BICHISMITA
NAMBOOTHIRI, IRISHI NN
PERSKY, RACHEL
 
Subject elimination
intermediates
synthesis
metal ions
 
Description 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.
 
Publisher Elsevier
 
Date 2009-02-14T16:52:07Z
2011-11-25T16:52:24Z
2011-12-26T13:05:34Z
2011-12-27T05:52:48Z
2009-02-14T16:52:07Z
2011-11-25T16:52:24Z
2011-12-26T13:05:34Z
2011-12-27T05:52:48Z
2005
 
Type Article
 
Identifier Tetrahedron Letters 46(15), 2593–2597
doi:10.1016/j.tetlet.2005.02.101
0040-4039
http://hdl.handle.net/10054/644
http://dspace.library.iitb.ac.in/xmlui/handle/10054/644
 
Language en