1449306-19-7Relevant articles and documents
New results on the photoreactivity of 5-fluoro-1,3-dimethyluracil with methoxylated naphthalenes
Ohkura, Kazue,Aizawa, Kazuya,Mukaida, Rie,Akizawa, Hiromichi,Seki, Koh-Ichi
, p. 1465 - 1481 (2012)
Photocycloaddition of 5-fluoro-1,3-dimethyluracil (5-FDMU) with various methoxy and dimethoxynaphthalenes was investigated. Reaction of 5-FDMU with 1,x-dimethoxynaphthalenes (x = 4-7) gave rise to the selective formation of cycloadducts, conjugated arylpropenylidene-1,3-diazin-2-ones, which were derived from an initially formed oxetane moiety via the Paterno-Buechi reaction cycloadduct. The present study shows that the presence of a methoxy substituent on the ?-position in naphthalene is essential for the formation of products through the Paterno-Buechi reaction. This unique photoreaction involving formation of an oxetane between 5-FDMU and a naphthalene ring, followed by a concomitant disruption of the initially formed oxetane moiety and an aromatic ring of naphthalene moiety, can be regarded as a novel aromatic Paterno-Buechi reaction.