Synthesis of arenediynes via the vinylidenecarbene-acetylene rearrangement
DSpace at IIT Bombay
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Title |
Synthesis of arenediynes via the vinylidenecarbene-acetylene rearrangement
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Creator |
SAHU, BICHISMITA
NAMBOOTHIRI, IRISHI NN PERSKY, RACHEL |
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Subject |
elimination
intermediates synthesis metal ions |
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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. |
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Publisher |
Elsevier
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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 |
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Type |
Article
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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 |
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Language |
en
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