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Synthesis of 2a,8b-Dihydrocyclobuta[<i>a</i>]naphthalene-3,4-diones

By Kerstin Schmidt and Paul Margaretha


On irradiation (&#955; = 350 nm) in neat hex-1-yne, naphthalene-1,2-dione monoacetals <b>1</b> afford mixtures of pentacyclic photodimers and up to 25% (isolated yield) of mixed photocycloadducts <b>2</b>. Careful acidic hydrolysis of the acetal function of <b>2</b> gives the title compounds <b>3</b>, the overall sequence representing a first approach to a (formal) [2 + 2] photocycloadduct of a 1,2-naphthoquinone to an alkyne

Topics: cyclobutenes, photocycloaddition, quinone monoacetals, Organic chemistry, QD241-441, Chemistry, QD1-999, Science, Q, DOAJ:Organic Chemistry, DOAJ:Chemistry
Publisher: Beilstein-Institut
Year: 2010
DOI identifier: 10.3762/bjoc.6.76
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