4,6-Dimethyl-o-quinone Methide and 4,6-Dimethylbenzoxete

4,6-Dimethyl-o-quinone methide (4) was produced by FVP of alcohol 3 or of the trimer 6 and matrix isolated in Ar at 7.6 K. Photolysis of 4 with long wavelength light (>345 nm) at this temperature afforded 4,6-dimethylbenzoxete (5), which was observable up to room temperature in the solid state in...

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Bibliographic Details
Published in:Journal of organic chemistry 1998-12, Vol.63 (26), p.9806-9811
Main Authors: Qiao, Greg GuangHua, Lenghaus, Keith, Solomon, David H, Reisinger, Ales, Bytheway, Ian, Wentrup, Curt
Format: Article
Language:English
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Summary:4,6-Dimethyl-o-quinone methide (4) was produced by FVP of alcohol 3 or of the trimer 6 and matrix isolated in Ar at 7.6 K. Photolysis of 4 with long wavelength light (>345 nm) at this temperature afforded 4,6-dimethylbenzoxete (5), which was observable up to room temperature in the solid state in the absence of water. 5 can be converted back to 4 by UV irradiation at 254/190 nm. Quantum chemical calculations on the thermal interconversion of 4 and 5 indicate activation barriers of the order of 40 kcal/mol for 4 → 5, and 30 kcal/mol for 5 → 4. The dimer, trimer, and tetramer (8, 6, and 7) of 4 are characterized.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo981445x