4
Tetrahedron
Scheme 6. Synthetic route to 3 via 10, 11, and 12.
In summary, regio-defined multiple introduction of hydroxyl
groups into a DBC core was successfully demonstrated. Key to
these single constructions were three: One, smooth dimerization
reactions of 9-fluorenone analogues readily prepared DBC
skeletons in 18-25 grams of laboratory-scale. Two, DBC
undertook direct tetra-bromination in perfectly regio-selective
manner. Three, the four bromines tethered DBC were all together
tolerable to Fleming-Tamao oxidation reactions. These three
simple findings enable us to separately make new multiple
hydroxyl DBC in pure form. This demonstration would be good
opportunity for understanding reactivity of DBC core and opening
the door of creating new functional organic materials anchored to
the DBC. Application to polymer assembly materials is ongoing
and will be reported in due course.
9
1
.
a) Makinoshima, T.; Echigo, M. PCT Int. Appl. (2015), WO
015170736 A1 20151112; b) Kato, H.; Takatori, M. Jpn. Kokai
Tokkyo Koho (2014), JP 2014152164 A 20140825; c) Kato, H.;
Takatori, M. Jpn. Kokai Tokkyo Koho (2013), JP 2013227307 A
Acknowledgments
2
Thankfully, this work was supported by 2019 the Joint
Research Center for Science and Technology of Ryukoku
University. The authors thank Dr. Toshiyuki Iwai and Dr.
Takatoshi Ito at ORIST for gentle assistance with HRMS. We are
grateful to Prof. Dr. Kiyosei Takasu, Dr. Yosuke Yamaoka, and
Mr. Naoki Ogawa at Kyoto University for helpful assistance of X-
ray diffraction and scattering.
2
1
0131107; c) Ohta, K. Jpn. Kokai Tokkyo Koho (2016), JP 2016-
25007 A 20160711.
0. a) Suzuki, N.; Fujita, T.; Ichikawa, J. Org. Lett. 2015, 17, 4984-
987; b) Ueda, Y.; Tsuji, H.; Tanaka, H.; Nakamura, E. Chem.
Asia. J. 2014, 1623-1628.
4
11. Commercially available dibenzo[g,p]chrysene (CAS# 191-68-4) in
Tokyo Chemical Industry Co., Ltd. is 1 g at the maximum amount
that costs us ¥ 44,000 (without tax).
1
2. a) Yamada, H.; Uchida, M. Jpn. Kokai Tokkyo Koho, (2011), JP
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