| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5280908 | Tetrahedron Letters | 2005 | 5 Pages |
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.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Bichismita Sahu, Irishi N.N. Namboothiri, Rachel Persky,