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   https://doi.org/10.1039/d1sc00158b  

   Zheng, Haifeng; Wang, Rui; Wang, Kan; Wherritt, Daniel; Arman, Hadi; Doyle, Michael P. (April 2021, Chemical Science)

   null (Ed.)

   Brønsted acid catalyzed formal [4 + 4]-, [4 + 3]-, and [4 + 2]-cycloadditions of donor–acceptor cyclobutenes, cyclopropenes, and siloxyalkynes with benzopyrylium ions are reported. [4 + 2]-cyclization/deMayo-type ring-extension cascade processes produce highly functionalized benzocyclooctatrienes, benzocycloheptatrienes, and 2-naphthols in good to excellent yields and selectivities. Moreover, the optical purity of reactant donor–acceptor cyclobutenes is fully retained during the cascade. The 1,3-dicarbonyl product framework of the reaction products provides opportunities for salen-type ligand syntheses and the construction of fused pyrazoles and isoxazoles that reveal a novel rotamer-diastereoisomerism. 

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3. Crystal structure of 4-methyl- N -(4-methylbenzyl)benzenesulfonamide

   https://doi.org/10.1107/S2056989020000535  

   Stenfors, Brock A.; Staples, Richard J.; Biros, Shannon M.; Ngassa, Felix N. (February 2020, Acta Crystallographica Section E Crystallographic Communications)

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   The title compound, C 15 H 17 NO 2 S, was synthesized via a substitution reaction between 4-methylbenzylamine and p -toluenesulfonyl chloride. In the crystal, N—H...O hydrogen bonds link the molecules, forming ribbons running along the b -axis direction. One of the aromatic rings hosts two intermolecular C—H...π interactions that link these hydrogen-bonded ribbons into a three-dimensional network. 

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5. Design, Synthesis and Aromaticity of an Alternating Cyclo[4]Thiophene[4]Furan

   https://doi.org/10.1002/chem.202300477  

   Kawakami, Manami; Sharma, Dhruv; Varni, Anthony_J; Tristram‐Nagle, Stephanie; Yaron, David; Kowalewski, Tomasz; Noonan, Kevin_J_T (May 2023, Chemistry – A European Journal)

   Abstract A new class of conjugated macrocycle, the cyclo[4]thiophene[4]furan hexyl ester (C4TE4FE), is reported. This cycle consists of alternating α‐linked thiophene‐3‐ester and furan‐3‐ester repeat units, and was prepared in a single step using Suzuki–Miyaura cross‐coupling of a 2‐(thiophen‐2‐yl)furan monomer. The ester side groups help promote asynconformation of the heterocycles, which enables formation of the macrocycle. Cyclic voltammetry studies revealed that C4TE4FE could undergo multiple oxidations, so treatment with SbCl₅resulted in formation of the [C4TE4FE]²⁺dication. Computational work, paired with¹H NMR spectroscopy of the dication, revealed that the cycle becomes globally aromatic upon 2e⁻oxidation, as the annulene pathway along the outer ring becomes Hückel aromatic. The change in ring current for the cycle upon oxidation was clear from¹H NMR spectroscopy, as the protons of the thiophene and furan rings shifted downfield by nearly 6 ppm. This work highlights the potential of sequence control in furan‐based macrocycles to tune electronic properties. 

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