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2013, Vol.42, No.12

1531-1533

Dimerization Reactions of 2-Bromo-3,5,6-trimethyl-1,4-benzoquinone

Shuhei Azuma 1 , Motohiro Ota 1 , Akito Ishida 1 , Katsuhiro Isozaki 2 , Hikaru Takaya 2 , Masaharu Nakamura 2 , Takahiro Sasamori 3 , Norihiro Tokitoh 3 , Kouji Kuramochi 1 , Kazunori Tsubaki 1
1 Graduate School of Life and Environmental Sciences, Kyoto Prefectural University
2 International Research Center for Elements Science (IRCELS), Institute for Chemical Research (ICR), Kyoto University
3 Institute for Chemical Research, Kyoto University
https://doi.org/10.1246/cl.130781

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Abstract
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The dimerization reactions of 2-bromo-3,5,6-trimethyl-1,4-benzoquinone have been examined. 2,2′-Dimeric benzoquinone was prepared via a Stille-type homocoupling, whereas an oxepin was formed by the treatment of the title quinone with hexamethylditin, CuI, and (±)-BINAP in DMF. Two dimerization reactions involving a hetero Diels–Alder reaction between quinones and quinone methides were also observed.

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