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Tuning Rate of the Bergman Cyclization of Benzannelated Enediynes with Ortho
 

Summary: Tuning Rate of the Bergman Cyclization
of Benzannelated Enediynes with Ortho
Substituents
Igor V. Alabugin,* Mariappan Manoharan, and Serguei V. Kovalenko
Department of Chemistry and Biochemistry, Florida State UniVersity,
Tallahassee, Florida 32306-4390
alabugin@chem.fsu.edu
Received January 2, 2002
ABSTRACT
The Bergman cyclization of benzannelated enediynes is highly sensitive to ortho substitution. This finding opens possibilities for the rational
design of conformer-specific and pH-dependent DNA-cleaving agents.
The thermal cyclization of (Z)-enediynes (the Bergman
cyclization)1 has a number of practical applications in the
design of DNA-cleaving agents,2 the development of poly-
meric materials with enhanced thermal properties,3and
synthesis of polycyclic compounds.4
Introduction of func-
tional groups in benzannelated enediynes can provide a
straightforward and synthetically viable way to control both
the cyclization rate and molecular recognition of the enediyne

  

Source: Alabugin, Igor - Department of Chemistry and Biochemistry, Florida State University

 

Collections: Chemistry; Biology and Medicine