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Synlett 1997; 1997(2): 165-166
DOI: 10.1055/s-1997-726
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Synthesis of Novel Enyne-Allenes, Their Thermal C2-C6 Cyclization, and the Importance of a Benzofulvene Biradical in the DNA Strand Cleavage1

Michael Schmittel* , Michael Maywald, Marc Strittmatter
  • *Institut für Organische Chemie der Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany, Fax: Int. +49 931 888 4606; e-mail: mjls@chemie.uni-wuerzburg.de
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Publication Date:
31 December 2000 (online)

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Novel enyne-allenes without acceptor substituents have been prepared from propargyl acetates by Pd-catalyzed addition of arylzinc chloride or by cuprate addition. Their thermal reaction afforded exclusively the C2-C6 and no Myers-Saite cyclization products. In one case, intermolecular hydrogen abstraction and DNA strand cleavage were observed.

enyne-allenes - zincate - cuprate - thermolysis - biradical cyclization