Sahu, Bichismita ; Namboothiri, Irishi N.N. ; Persky, Rachel (2005) Synthesis of arenediynes via the vinylidenecarbene–acetylene rearrangement Tetrahedron Letters, 46 (15). pp. 2593-2597. ISSN 0040-4039
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Official URL: http://doi.org/10.1016/j.tetlet.2005.02.101
Related URL: http://dx.doi.org/10.1016/j.tetlet.2005.02.101
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 121599 |
| Deposited On: | 19 Jul 2021 11:28 |
| Last Modified: | 19 Jul 2021 11:28 |
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