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Skeletal Rearrangem...
Skeletal Rearrangement of Twisted Thia-Norhexaphyrin : Multiply Annulated Polypyrrolic Aromatic Macrocycles
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- Li, Qizhao (author)
- East China Univ Sci & Technol, Key Lab Adv Mat, Feringa Nobel Prize Scientist Joint Res Ctr, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Joint Int Res Lab Precis Chem & Mol Engn, Feringa Nobel Prize Scientist Joint Res Ctr, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China.
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- Ishida, Masatoshi (author)
- Kyushu Univ, Dept Chem & Biochem, Grad Sch Engn, Fukuoka 8190395, Japan.;Kyushu Univ, Ctr Mol Syst, Fukuoka 8190395, Japan.
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- Kai, Hiroto (author)
- Kyushu Univ, Dept Chem & Biochem, Grad Sch Engn, Fukuoka 8190395, Japan.;Kyushu Univ, Ctr Mol Syst, Fukuoka 8190395, Japan.
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- Gu, Tingting (author)
- Jiangsu Univ, Sch Chem & Chem Engn, Zhenjiang 212013, Jiangsu, Peoples R China.
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- Li, Chengjie (author)
- East China Univ Sci & Technol, Key Lab Adv Mat, Feringa Nobel Prize Scientist Joint Res Ctr, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Joint Int Res Lab Precis Chem & Mol Engn, Feringa Nobel Prize Scientist Joint Res Ctr, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China.
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- Li, Xin (author)
- KTH,Parallelldatorcentrum, PDC,Teoretisk kemi och biologi
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- Baryshnikov, Glib (author)
- KTH,Teoretisk kemi och biologi
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- Liang, Xu (author)
- Jiangsu Univ, Sch Chem & Chem Engn, Zhenjiang 212013, Jiangsu, Peoples R China.
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- Zhu, Weihua (author)
- Jiangsu Univ, Sch Chem & Chem Engn, Zhenjiang 212013, Jiangsu, Peoples R China.
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- Ågren, Hans (author)
- KTH,Teoretisk kemi och biologi,Dept Theoret Chem & Biol, Sch Biotechnol, S-10691 Stockholm, Sweden.
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- Furuta, Hiroyuki (author)
- Kyushu Univ, Dept Chem & Biochem, Grad Sch Engn, Fukuoka 8190395, Japan.;Kyushu Univ, Ctr Mol Syst, Fukuoka 8190395, Japan.
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- Xie, Yongshu (author)
- East China Univ Sci & Technol, Key Lab Adv Mat, Feringa Nobel Prize Scientist Joint Res Ctr, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Joint Int Res Lab Precis Chem & Mol Engn, Feringa Nobel Prize Scientist Joint Res Ctr, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China.
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East China Univ Sci & Technol, Key Lab Adv Mat, Feringa Nobel Prize Scientist Joint Res Ctr, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China;East China Univ Sci & Technol, Joint Int Res Lab Precis Chem & Mol Engn, Feringa Nobel Prize Scientist Joint Res Ctr, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China. Kyushu Univ, Dept Chem & Biochem, Grad Sch Engn, Fukuoka 8190395, Japan.;Kyushu Univ, Ctr Mol Syst, Fukuoka 8190395, Japan. (creator_code:org_t)
- WILEY-V C H VERLAG GMBH, 2019
- 2019
- English.
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In: Angewandte Chemie International Edition. - : WILEY-V C H VERLAG GMBH. - 1433-7851 .- 1521-3773. ; 58:18, s. 5925-5929
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- A hybrid thia-norhexaphyrin comprising a directly linked N-confused pyrrole and thiophene unit (1) revealed unique macrocycle transformations to afford multiply inner-annulated aromatic macrocycles. Oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone triggered a cleavage of the C-S bond of the thiophene unit, accompanied with skeletal rearrangement to afford unique pi-conjugated products: a thiopyrrolo-pentaphyrin embedded with a pyrrolo[1,2]isothiazole (2), a sulfur-free pentaphyrin incorporating an indolizine moiety (3), and a thiopyranyltriphyrinoid containing a 2H-thiopyran unit (4). Furthermore, 2 underwent desulfurization reactions to afford a fused pentaphyrin containing a pyrrolizine moiety (5) under mild conditions. Using expanded porphyrin scaffolds, oxidative thiophene cleavage and desulfurization of the hitherto unknown N-confused core-modified macrocycles would be a practical approach for developing unique polypyrrolic aromatic macrocycles.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- aromaticity
- macrocycles
- porphyrinoids
- skeletal rearrangement
Publication and Content Type
- ref (subject category)
- art (subject category)
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- By the author/editor
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Li, Qizhao
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Ishida, Masatosh ...
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Kai, Hiroto
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Gu, Tingting
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Li, Chengjie
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Li, Xin
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Baryshnikov, Gli ...
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Liang, Xu
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Zhu, Weihua
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Ågren, Hans
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Furuta, Hiroyuki
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Xie, Yongshu
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- About the subject
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Chemical Science ...
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and Organic Chemistr ...
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Angewandte Chemi ...
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Royal Institute of Technology