CuCl-induced formation and migration of isoindazolyl carbenoids.
Two azo-ene-butadiyne conjugated systems undergo CuCl-mediated cyclization to afford isoindazolyl carbenoids that could be trapped with 2,3-dimethyl-2-butene as [2+1] cycloaddition products. X-ray structure analysis of the resultant cyclopropanes showed that formal migration to the distal carbenoid isomer and subsequent trapping had occurred. The possible CuCl-induced cyclization/migration pathways were explored using density functional theory, which indicated that the reaction most likely occurred via coordination of CuCl to the distal alkyne bond.
Shirtcliff
Laura D
LD
Department of Chemistry, University of Oregon, Eugene, Oregon 97403-1253, USA.
Haley
Michael M
MM
Herges
Rainer
R
D001391:Azo Compounds / Q000737:chemistry; D003201:Computers; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry; D053280:Diynes / Q000737:chemistry; D006838:Hydrocarbons / Q000737:chemistry; D007191:Indazoles / Q000737:chemistry*; D007536:Isomerism; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure
D001391:Azo Compounds; D003521:Cyclopropanes; D053280:Diynes; D006838:Hydrocarbons; D007191:Indazoles; C030011:carbene; D003300:Copper; C030797:cyclopropane; D008697:Methane; C029892:cupric chloride