Synthesis of arenediynes via the vinylidenecarbene-acetylene rearrangement

Bichismita Sahu, Irishi N.N. Namboothiri, Rachel Persky

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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.

Original languageEnglish
Pages (from-to)2593-2597
Number of pages5
JournalTetrahedron Letters
Volume46
Issue number15
DOIs
StatePublished - 11 Apr 2005

Bibliographical note

Funding Information:
The authors thank DST, India, for financial assistance and SAIF, IIT Bombay, for NMR data. B.S. thanks CSIR, India, for a scholarship.

Keywords

  • Enediynes
  • Fritsch-Buttenberg-Wiechell rearrangement
  • Vinylidenecarbene

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