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Synthesis of 2-substituted quinones, vitamin K3, and vitamin K1 from p-cresol. BF3·OEt2-catalyzed methyl migration of 4-tert-butyldioxycyclohexadienones

✍ Scribed by Shun-Ichi Murahashi; Akiko Fujii; Yasutaka Inubushi; Naruyoshi Komiya


Book ID
104097555
Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
466 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis


BF 3 ÁOEt 2 -catalyzed methyl group migration of 4-methyl-4-tert-butyldioxycyclohexadienone, which is obtained by ruthenium-catalyzed oxidation of p-cresol with tert-butyl hydroperoxide, in hexafluoro-2propanol/toluene gave toluquinone efficiently. The reaction can be applied to the regio-selective shortstep syntheses of vitamin K 3 and vitamin K 1 from p-cresol.


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