Synthesis of arenediynes via the vinylidenecarbene-acetylene rearrangement |
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Authors: | Bichismita Sahu Rachel Persky |
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Affiliation: | a Department of Chemistry, Indian Institute of Technology, Bombay, Mumbai 400 076, India b Department of Chemistry, Bar-Ilan University, Ramat Gan 52900, Israel |
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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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Keywords: | Enediynes Vinylidenecarbene Fritsch-Buttenberg-Wiechell rearrangement |
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