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A novel solvent effect in the dye-sensitized photooxidation of [2.2] (2,5) furanophane

โœ Scribed by H.H. Wasserman; R. Kitzing

Publisher
Elsevier Science
Year
1969
Tongue
French
Weight
158 KB
Volume
10
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

In a previous investigation1 we have reported that the dye-sensitized photwxidation of [2.21 (2.5)furanophane (I) in methanol leads to an oxygenated intermediate which underqoes an 2 intramolecular Diels-Alder reaction forming the diketone (II) .

We have now observed that this oxidation reaction takes a different course when the sol-* vent is changed from methanol to methylene chloride.

Thus, when I is irradiated in freshly distilled methylene chloride (150 watt photoflood lamp, methylene blue) for 16 hr. while oxygen is bubbled through the solution, a new product (75%) gradually precipitates. This product, showinq no carbonyl or hydroxyl absorption in the infrared, melts at Ml-182O with vigorous decomposition, and exhibits a parent peak in the mass spectrum at m/e 252. Anal.

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