Title: Wavelength-Dependent Photochemistry of Diazo Meldrum's Acid and Its Spirocyclic Isomer, Diazirino Meldrum's Acid: Wolff Rearrangement versus Isomerization
Abstract: Photoreaction of diazo Meldrum's acid (1) shows a unique wavelength selectivity. At 254 nm it results in efficient (φ254 = 0.34) Wolff rearrangement, while irradiation with 355 nm light leads to a completely different process, isomerization into corresponding cyclic α,α''-dicarbonyl diazirine 2 (φ350 = 0.024). UV photolysis of diazirine 2 is accompanied by two competing processes: loss of nitrogen followed by the Wolff rearrangement and isomerization into diazo compound 1. Thermal decomposition of 1 leads to clean Wolff rearrangement, while heating of 2 causes quantitative conversion into diazo isomer 1.
Publication Year: 2003
Publication Date: 2003-01-16
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
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Cited By Count: 31
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