Oxidation of a triple carbo[5]helicene with hypervalent iodine
Literature Information
Publication Date
2023-10-12
DOI
10.1039/D3QO01439H
Impact Factor
5.281
Authors
Florian Rigoulet, Albert Artigas, Nawal Ferdi, Michel Giorgi, Yoann Coquerel
View Original
Abstract
The reactivities of both diastereomers of hexabenzotriphenylene (HBTP), a triple carbo[5]helicene of the formula C42H24, were examined in the presence of phenyliodine diacetate (PIDA) as an oxidizing agent. The D3-symmetric diastereomer afforded two different ring rearranged ketone-containing products embedding a spirofluorene moiety. In contrast, under similar conditions, the C2-symmetric diastereomer afforded predominantly a cyclodehydrogenation product. Altogether, this shows that stereochemistry is a critical factor in the reactivity of non-planar polycyclic aromatic hydrocarbons.
Related Literature
An effective preparation of both 1,3-diketones and nitriles from alkynones with oximes as hydroxide sources
Pei Chen, Qian-Qian Zhang, Jia Guo, Lu-Lu Chen, Yan-Bo Wang, Xiao Zhang
2018-09-03
Paper
DOI: 10.1039/C8OB01861H
A stereodivergent, two-directional synthesis of stereoisomeric C-linked disaccharide mimetics
Michael Harding, Robert Hodgson, Tahir Majid, Kenneth J. McDowall
2002-12-17
Paper
DOI: 10.1039/B208781B
Hydride-exchange reactions between NADH and NAD+ model compounds under non-steady-state conditions. Apparent and real kinetic isotope effects
Yun Lu, Yixing Zhao, Kishan L. Handoo, Vernon D. Parker
2002-11-22
Paper
DOI: 10.1039/B208186E
Optimized synthesis and indium complex formation with the bifunctional chelator NODIA-Me
Jason P. Holland, Harald Scherer, Stephan Maus, Tobias Stemler, Hendrik Bohnenberger, Samer Ezziddin, Philipp Kurz
2018-09-24
Paper
DOI: 10.1039/C8OB01981A
Refined methods for the synthesis of meso-substituted A3- and trans-A2B-corroles
Daniel T. Gryko, Beata Koszarna
2002-12-09
Paper
DOI: 10.1039/B208950E
A convergent approach to the marine natural product eleutherobin: synthesis of key intermediates and attempts to produce the basic skeleton
Gaia Scalabrino, Xiao-Wen Sun, John Mann, Anne Baron
2002-12-13
Paper
DOI: 10.1039/B207800G
UV light-driven asymmetric vinylogous aldol reaction of isatins with 2-alkylbenzophenones and enantioselective synthesis of 3-hydroxyoxindoles
Shixuan Cao, Jiatian Li, Taishan Yan, Jie Han
2021-12-07
Research Article
DOI: 10.1039/D1QO01555A
Asymmetric fluorination of indanone-2-carboxylates using a polystyrene-supported diphenylamine-linked bis(oxazoline) complex
Biao Wang, Yifeng Wang, Yidong Jiang, Mingming Chu, Suosuo Qi, Wanzhen Ju, Danqian Xu
2018-09-28
Paper
DOI: 10.1039/C8OB01943F
Preferential precipitation of C70 over C60 with p-halohomooxacalix[3]arenes
Naoki Komatsu
2002-11-27
Paper
DOI: 10.1039/B208107E
Ru-Catalyzed dehydrogenative synthesis of antimalarial arylidene oxindoles
Girish Singh Bisht, Akanksha M. Pandey, Moreshwar B. Chaudhari, Sandip G. Agalave, Abhishek Kanyal, Krishanpal Karmodiya, Boopathy Gnanaprakasam
2018-09-18
Paper
DOI: 10.1039/C8OB01852A
You might also like
Compound Q&A
What is the market or research trend for N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0)?
N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0) is increasingly being used ...
52818-63-0N-(4-Methoxybenzyl)-...
Compound Q&A
What precautions should be taken when handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate (CAS: 1050507-06-6)?
When handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate, appropriate p...
1050507-06-6Ethyl 4-(2-chlorophe...
Compound Q&A
What regulatory guidelines apply to diethyldiselane (CAS: 628-39-7)?
Diethyldiselane (CAS: 628-39-7) is classified under the Globally Harmonized Syst...
628-39-7Diethyldiselane
Compound Q&A
What is the market or research trend for oxocopper (CAS: 12053-18-8)?
The market for oxocopper (CAS: 12053-18-8) is primarily driven by its use in cat...
12053-18-8oxocopper; oxo-(oxoc...
Compound Q&A
What is the market or research trend for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-carboxylic acid?
The market for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-c...
1268519-54-55-{[(2-Methyl-2-prop...
Compound Q&A
What is 2-(1-Pyrrolidinyl)-4-pyridinamine (CAS: 35981-63-6)?
2-(1-Pyrrolidinyl)-4-pyridinamine is a chemical compound with the CAS number 359...
35981-63-62-(1-Pyrrolidinyl)-4...
Compound Q&A
What are the physical and chemical properties of 2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1)?
2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1) is a crystalline sol...
91556-75-12-(3-Pyridinyl)-1-az...
Compound Q&A
How is (S)-Alpha-allyl-proline hydrochloride (CAS: 129704-91-2) typically synthesized?
(S)-Alpha-allyl-proline hydrochloride is usually synthesized via a Wittig reacti...
129704-91-2(S)-Alpha-allyl-prol...
Compound Q&A
What is 3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5)?
3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5) is an organic compound w...
4857-42-53-Methyl-1,2-oxazole...
Compound Q&A
How is Lys-SMCC-DM1 (CAS: 1281816-04-3) typically synthesized?
Lys-SMCC-DM1 is synthesized via a multi-step process involving the coupling of S...
1281816-04-3Lys-SMCC-DM1
Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
N-Methyl-3-(1-naphthyloxy)-3-(2-thienyl)-1-propanamine hydrochloride (1:1)
CAS Number:
1188266-11-6
Molecular Formula:
C18H20ClNOS
![1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone structure](https://static.chemtradehub.com/structs/122/1226872-27-0-e037.webp "1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone structure")
1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone
CAS Number:
1226872-27-0
Molecular Formula:
C25H26N6O4
Recommended Suppliers
Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.