Tetrahedron letters

Synthesis of arenediynes via the vinylidenecarbene–acetylene rearrangement

B Sahu, INN Namboothiri, R Persky

文献索引：Sahu, Bichismita; Namboothiri, Irishi N.N.; Persky, Rachel Tetrahedron Letters, 2005 , vol. 46, # 15 p. 2593 - 2597

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被引用次数: 11

摘要

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 ...