(1) (a) Berresheim, A. J.; Müllen, K. Polyphenylene Nanostructures. Chem. Rev. 1999, 99, 1747−1786. (b)
Watson, M. D.; Fechtenkötter, A.; Müllen, K. Big Is Beautiful−“Aromaticity” Revisited from the
Viewpoint of Macromolecular and Supramolecular Benzene Chemistry. Chem. Rev. 2001, 101, 1267−1300.
(c) Bendikov, M.; Wudl, F.; Perepichka, D. F. Tetrathiafulvalenes, Oligoacenenes, and Their
Buckminsterfullerene Derivatives: The Brick and Mortar of Organic Electronics. Chem. Rev. 2004, 104,
4891−4945. (d) Anthony, J. E. The larger Acenes: Versatile Organic Semiconductors. Angew. Chem., Int.
Ed. 2008, 47, 452−483. (e) Figueira-Duarte, T. M.; Müllen, K. Pyrene-Based Materials for Organic
Electronics. Chem. Rev. 2011, 111, 7260−7314. (f) Sun, Z.; Ye, Q.; Chi, C.; Wu, J. Low Band Gap Polycyclic
Hydrocarbons: From Closed-Shell Near Infrared Dyes and Semiconductors to Open-Shell Radicals. Chem.
Soc. Rev. 2012, 41, 7857−7889. (g) Jiang, W.; Li, Y.; Wang, Z.-H. Heteroarenes as High Performance
Organic Semiconductors. Chem. Soc. Rev. 2013, 42, 6113−6127.
A Self-archived copy in
Kyoto University Research Information Repository
https://repository.kulib.kyoto-u.ac.jp
(2) (a) Pashin, Y. V.; Bakhitova, L. M. Mutagenic and Carcinogenic Properties of Polycyclic Aromatic
Hydrocarbons. Environ. Health Perspect. 1979, 185−189. (b) da Silva Junior, F. C.; Felipe, M. B. M. C.;
de Castro, D. E. F.; da Silva Araújo, S. C.; Sisenando, H. C. N.; de Medeiros, S. R. B. A. Look beyond the
Priority: A systematic Review of the Genotoxic, Mutagenic, and Carcinogenic Endpoints of Non-priority
PAHs. Environ. Pollut. 2021, 278, 116838.
(3) Mohan, S. B.; Kumar, V. R.; Venkata, B.; Krishna, B. B.; Preetismita, B. Polyaromatic Hydrocarbons
(PAHs): Structures, Synthesis and Biological Profile. Curr. Org. Synth. 2020, 17, 625−640.
(4) (a) Niko, Y.; Hiroshige, Y.; Kawauchi, S.; Konishi, G.-i. Additional Insights into Luminescence Process
of Polycyclic Aromatic Hydrocarbons with Carbonyl Groups: Photophysical Properties of Secondary NAlkyl and Tertiary N,N-Dialkyl Carboxamides of Naphthalene, Anthracene, and Pyrene. J. Org. Chem.
2012, 77, 3986−3996. (b) Achten, C.; Andersson, J. T. Overview of Polycyclic Aromatic Compounds (PAC).
Polycyclic Aromat. Compd. 2015, 35, 177−186. (c) Kroonblawd, M. P.; Lindsey, R. K.; Goldman, N.
Synthesis of Functionalized Nitrogen-containing Polycyclic Aromatic Hydrocarbons and Other Prebiotic
Compounds Impacting Glycine Solutions. Chem. Sci. 2019, 10, 6091−6098. (d) Yang, X.; Hoffmann, M.;
Rominger, F.; Kirchbaum, T.; Dreuw, A.; Mastalerz, M. Functionalized Contorted Polycyclic Aromatic
Hydrocarbons by a One-step Cyclopentannulation and Regioselective Triflyoxylation. Angew. Chem., Int.
Ed. 2019, 58, 10650−10654.
(5) Nagamoto, Y.; Yamaoka, Y.; Fujimura, S.; Takemoto, Y.; Takasu, K. Synthesis of Functionalized
Polycyclic Aromatic Compounds via a Formal [2 + 2]-Cycloaddition. Org. Lett. 2014, 16, 1008−1011.
(6) (a) Nagamoto, Y.; Hattori, A.; Kakeya, H.; Takemoto, Y.; Takasu, K. pH-Sensitive DNA Cleaving
Agents: In situ Activation by Ring Contraction of Benzo-fused Cyclobutanols. Chem. Commun. 2013, 49,
2622−2624. (b) Yamaoka, Y.; Taniguchi, M.; Yamada, K.; Takasu, K. Asymmetric Total Synthesis of
Tylophorine via a Formal [2+2] Cycloaddition Followed by Migrative Ring Opening of a Cyclobutane.
Synthesis 2015, 47, 2819−2825. (c) Yamaoka, Y.; Taniguchi, M.; Yamada, K.; Takasu, K. Total Synthesis
of Phenanthroquinolizidine Alkaloid Cryptopleurine and Phenanthroindolizidine Alkaloid Tylophorine.
Heterocycles 2018, 97, 292−305. (d) Ogawa, N.; Yamaoka, Y.; Takikawa, H.; Takasu, K. Synthesis of
A Self-archived copy in
Kyoto University Research Information Repository
https://repository.kulib.kyoto-u.ac.jp
Polycyclic Spirocarbocyles via Acid-Promoted Ring-Contraction/Dearomative Ring-Closure Cascade of
Oxapropellanes. Org. Lett. 2019, 21, 7563−7567.
(7) Ogawa, N.; Yamaoka, Y.; Takikawa, H.; Tsubaki, K.; Takasu, K. Synthesis and Properties of
Tribenzocarbazoles via an Acid-Promoted Retro (2+2)-Cycloaddition of Azapropellanes. J. Org. Chem.
2018, 83, 7994−8002.
(8) Selected examples for the synthesis PAHs from cyclobutanols: (a) Yu, J.; Yan, H.; Zhu, C. Synthesis
of Multiply Substituted Polycyclic Aromatic Hydrocarbons by Iridium-Catalyzed Annulation of RingFused Benzocyclobutenol with Alkyne through C−C Bond Cleavage. Angew. Chem. Int. Ed. 2016, 55,
1143−1146. (b) Mao, Y.; Zhu, C. C–C Bond (Hetero)arylation of Ring-Fused Benzocyclobutenols and
Application in the Assembly of Polycyclic Aromatic Hydrocarbons. J. Org. Chem. 2017, 82, 9133−9143.
(9) Selected reviews: (a) Marek, I.; Masarwa, A.; Delaye, P.-O.; Liebeling, M. Selective Carbon-Carbon
Bond Cleavage for Stereoselective Synthesis of Acyclic Systems. Angew. Chem., Int. Ed. 2015, 54,
414−429. (b) Ren, R.; Zhu, C. Radical-Mediated Ring-Opening Functionalization of Cyclobutanols: A
Shortcut to g-Substituted Ketones. Synlett 2016, 1139−1144. (c) Murakami, M.; Ishida, N. b-Scission of
Alkoxy Radicals in Synthetic Transformations. Chem. Lett. 2017, 46, 1692−1700. (d) Wu, X.; Zhu, C.
Recent Advances in Ring-Opening Functionalization of Cycloalkanols by C-C σ-Bond Cleavage. Chem.
Rec. 2018, 18, 587−598. (e) Wu, X.; Zhu, C. Recent Advances in Alkoxy Radical-Promoted C-C and CH bond Functionalization Starting from Free Alcohols. Chem. Commun. 2019, 55, 9747−9756.
(10) Selected examples. (a) Kobayashi, K.; Itoh, M.; Suginome, H. A New Synthesis of Phthalides through
-Scission of Benzocyclobutenol Hypoiodites. Tetrahedron Lett. 1987, 28, 3369−3372. (b) Suginome, H.;
Takeda, T.; Itoh, M.; Nakayama, Y.; Kobayashi, K. Photoinduced Molecular Transformations. Part 152.
Ring Expansion Based on a Sensitized [2 + 2] Photoaddition of Enol Ethers of Cyclic Ketones with Olefins,
Followed by a -Scission of Alkoxy Radicals Generated from the Resulting Cyclobutanols. Two-Carbon
Ring Expansion of -Indanone, -Tetralone and -Suberone. J. Chem. Soc., Perkin Trans. 1 1995, 49−61.
(c) Uemura, S.; Ohe, K.; Nishimura, T. Oxidative Transformation of tert-Cyclobutanols by Palladium
Catalysis under Oxygen Atmosphere. J. Org. Chem. 2001, 66, 1455−1465. (d) Takasu, K.; Nagao, S.; Ihara,
A Self-archived copy in
Kyoto University Research Information Repository
https://repository.kulib.kyoto-u.ac.jp
M. Synthesis of Medium-sized -Haloketones by Radical Mediated Ring-opening Reaction of Lewis Acid
Catalyzed (2+2)-Cycloadducts. Tetrahedron Lett. 2005, 46, 1005−1008. (e) Fujioka, H.; Komatsu, H.;
Miyoshi, A.; Murai, K.; Kita, Y. Phenyliodine Diacetate-Mediated Oxidative Cleavage of Cyclobutanols
Leading to -Hydroxy Ketones. Tetrahedron Lett. 2011, 52, 973−975. (f) Ren, R.; Zhao, H.; Huan, L.; Zhu,
C. Manganese-Catalyzed Oxidative Azidation of Cyclobutanols: Regiospecific Synthesis of Alkyl Azides
by C-C Bond Cleavage. Angew. Chem., Int. Ed. 2015, 54, 12692−12696. (g) Kurouchi, H.; Andujar-De
Sanctis I. L.; Singleton D. A. Controlling Selectivity by Controlling Energy Partitioning in a Thermal
Reaction in Solution. J. Am. Chem. Soc. 2016, 138, 14534-14537. (h) Huan, L.; Zhu, C. ManganeseCatalyzed Ring-Opening Chlorination of Cyclobutanols: Regiospecific Synthesis of -Chloroketones. Org.
Chem. Front. 2016, 3, 1467−1471. (i) Lopez, M. M.; Jamey, N.; Pinet, A.; Figadere, B.; Ferrié, L. Oxidative
Ring Expansion of Cyclobutanols: Access to Functionalized 1,2-Dioxanes, Org. Lett. 2021, 23, 1626−1631.
(11) Kirihara, M.; Okada, T.; Sugiyama, Y.; Akiyoshi, M.; Matsunaga, T.; Kimura, Y. Sodium Hypochlorite
Pentahydrate Crystals (NaOCl∙5H2O): A Convenient and Environmentally Benign Oxidant for Organic
Synthesis. Org. Proc. Res. Dev. 2017, 21, 1925−1937.
(12) (a) Yin, Q.; Wang, S.-G.; Liang, X.-W.; Gao, D.-W.; Zheng, J.; You, S.-Li. Organocatalytic Asymmetric
Dearomatization of Naphthols. Chem. Sci. 2015, 6, 4179−4183. (b) Wang, P.; Wang, J.; Wang, L.; Li, D.;
Wang, K.; Liu, Y.; Zhu, H.; Liu, X.; Yang, D.; Wang.; L. Asymmetric Dearomative Halogenation of bNaphthols: The Axial Chirality Transfer Reaction. Adv. Synth. Catal. 2018, 360, 401−405. (c) Uyanik, M.;
Sahara, N.; Ishihara, K. Regioselective Oxidative Chlorination of Arenols Using NaCl and Oxone. Eur. J.
Org. Chem. 2019, 27−31.
...