27179-99-3Relevant academic research and scientific papers
LiAIH4 promoted reductive deoxygenation of hydroxybenzyl alcohols via benzoquinone methide intermediates
Baik, Woonphil,Lee, Hyun Joo,Koo, Sangho,Kim, Byeong Hyo
, p. 8125 - 8128 (1998)
Primary and secondary hydroxybenzyl alcohols react with LiAIH4 in chlorobenzene to give the corresponding alkylphenols. The reaction proceeds through the formation of benzoquinone methide as an intermediate. An example of [4+2] cycloaddition of benzoquinone methide is also reported.
4,6-Dimethyl-o-quinone methide and 4,6-dimethylbenzoxete
Guang, Greg,Qiao, Hua,Lenghaus, Keith,Solomon, David H.,Reisinger, Ales,Bytheway, Ian,Wentrup, Curt
, p. 9806 - 9811 (2007/10/03)
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.
