Abstract
Solution phase photolysis of the Diels-Alder adduct 3 formed between o-quinodimethane and 2,3-dimethyl-1,4-naphthoquinone affords, via β-hydrogen atom abstraction and closure of the resulting 1,3-biradical, the cyclopropanol 4. The cyclopropanol itself undergoes secondary photolysis initiated by a novel ring opening process. Irradiation of crystals of adduct 3 affords no detectable photoproducts. The crystal and molecular structure of 3 reveals that cyclopropanol formation in the solid state would involve prohibitive non-bonded steric interactions between lattice neighbors.
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