Solvent-dependent stereoselectivity of bis-2-pyridone [4 + 4] photocycloaddition is due to H-bonded dimers.
[formula: see text] A solvent-dependent stereoselectivity found for intramolecular [4 + 4] photocycloaddition of tethered 2-pyridones is concentration dependent, indicating that a dimeric structure with four hydrogen bonds plays a critical role in the observed cis selectivity found for nonpolar solvents.
Sieburth
S M
SM
Department of Chemistry, State University of New York, Stony Brook 11794-3400, USA. ssieburth@sunysb.edu
McGee
K F
KF
D003500:Cyclization; D019281:Dimerization; D006860:Hydrogen Bonding; D008027:Light; D008958:Models, Molecular; D008968:Molecular Conformation; D011728:Pyridones / Q000737:chemistry* / Q000528:radiation effects; D012997:Solvents; D013237:Stereoisomerism
D011728:Pyridones; D012997:Solvents