Photoreactivity of 2-pyridones with furan, benzene, and naphthalene. Inter- and intramolecular photocycloadditions.
Pyridones, well-known for their ability to photodimerize, have been found to undergo [4 + 4] photocycloaddition with furan and naphthalene but not with benzene. In some cases these reactions can be highly regio- and stereospecific. Intramolecular reaction with furan produces both cis and trans [4 + 4] products. The cycloaddition with naphthalene can occur both inter- and intramolecularly. The intermolecular reaction yields primarily the cis isomer, whereas the trans isomer is the major product from the intramolecular reaction. A mixture of 4-methoxy-2-pyridone and 2-methoxynaphthalene that could form up to eight regio- and stereoisomers forms largely one [4 + 4] product.
Sieburth
S M
SM
Department of Chemistry, State University of New York, Stony Brook 11794-3400, USA. scott.sieburth@sunysb.edu
McGee
K F
KF
Zhang
F
F
Chen
Y
Y
D001554:Benzene / Q000737:chemistry; D003500:Cyclization; D005663:Furans / Q000737:chemistry; D006865:Hydrogenation; D009682:Magnetic Resonance Spectroscopy; D009281:Naphthalenes / Q000737:chemistry; D010777:Photochemistry; D011728:Pyridones / Q000737:chemistry*
D005663:Furans; D009281:Naphthalenes; D011728:Pyridones; D001554:Benzene