Electronic control of the Bergman cycloaromatization: synthesis and chemistry of chloroenediynes.
[reaction: see text] A series of cyclic mono- and dichloroenediynes have been prepared using an intramolecular carbenoid coupling reaction. The halogen atom had a retardative effect on Bergman cycloaromatization in every case examined, and atom transfer chemistry was demonstrated, resulting in formation of adducts.
Jones
G B
GB
Bioorganic and Medicinal Chemistry Laboratories, Department of Chemistry, Northeastern University, Boston, MA 02115, USA. grjones@lynx.neu.edu
Plourde II
G W
GW
D000480:Alkynes / Q000737:chemistry; D004249:DNA Damage; D004277:DNA, Single-Stranded / Q000378:metabolism; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry
D000480:Alkynes; D004277:DNA, Single-Stranded; D006841:Hydrocarbons, Aromatic; D006843:Hydrocarbons, Chlorinated