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Journal articles on the topic 'Crystal engineering [2+2] cycloaddition'

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Published: 5 June 2025

Last updated: 1 August 2025

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1

Basudeb, Dutta, Sinha Chittaranjan, and Hedayetullah Mir Mohammad. "Exploration of [2+2] photodimerization of coordination polymers in various applications." Journal of Indian Chemical Society Vol. 97, No. 12a, Dec 2020 (2020): 2601–7. https://doi.org/10.5281/zenodo.5655912.

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Department of Chemistry, Aliah University, New Town, Kolkata-700 160, India Department of Chemistry, Jadavpur University, Jadavpur, Kolkata-700 032, India <em>E-mail: </em>crsjuchem@gmail.com, chmmir@gmail.com <em>Manuscript received online 10 November 2020, revised and accepted 23 December 2020</em> The exploration of coordination polymers (CPs) composed of metal ion and organic ligand has been incipient at an astonishing pace. The promising applications and essential diversity in structure of these materials are the driving forces behind the extensive research of such kind. Actually, inorgan

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Mohammad, Hedayetullah Mir, Dutta Basudeb, Islam Sakhiul, and Khan Samim. "Solid-state photodimerization via [2+2] cycloaddition in metal complexes and CPs." Journal of Indian Chemical Society Vol. 96, Oct 2019 (2019): 1297–301. https://doi.org/10.5281/zenodo.5642582.

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Department of Chemistry, Aliah University, New Town, Kolkata-700 160, India <em>E-mail</em>: chmmir@gmail.com <em>Manuscript received online 22 October 2019, accepted 23 October 2019</em> Coordination polymers (CPs) are made by the metal ions connecting the organic molecules at regular intervals in the polymer chain. CPs have high crystallinity, multi-dimensional structures, and are made by self-assembly. For last few decades, this active research area has become very much attractive to materials researchers due to the modular design, interesting properties and potential applications of CPs in

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3

Tan, Zeqing, Jian Zhao, Jingzhi Sun, et al. "CHCl3-Dependent Emission Color and Jumping Behavior of Cyclic Chalcone Single Crystals: The Halogen Bond Network Effect." Crystals 11, no. 5 (2021): 530. http://dx.doi.org/10.3390/cryst11050530.

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As a conventional strategy to modulate the structure and properties of inorganic single crystals, hydration/solvation is rarely found to function in pure organic single crystal. Herein, we report chalcone single crystals with CHCl3-dependent emission color and jumping behavior. Two crystals: a pure crystal phase (1) with green-yellow emission and a CHCl3-containing co-crystal phase (1•2CHCl3) with orange-red emission were constructed by fine-controlling the crystallization conditions. The special halogen bond network in the crystal packing structure effectively narrows the bandgap and thereby

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4

Vologzhanina, Anna V., Dmitry Yu Aleshin, Alexander D. Volodin, Anton V. Savchenkov, Ivan E. Ushakov, and Alexander A. Korlyukov. "Solid-State Photoinitiated Cycloaddition Reaction of 4,4′-(Ethene-1,2-diyl)bis(pyridinium) Dinitrate: Charge-Density Perspective on Initial Stage of the Reaction." Crystals 9, no. 12 (2019): 613. http://dx.doi.org/10.3390/cryst9120613.

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Solid-state photoinitiated [2 + 2] cycloaddition reaction 2(H2bpe)(NO3)2 → (H4tpcb)(NO3)4 (bpe = 1,2-bis(pyrid-4-yl)ethylene; tpcb = 1,2,3,4-tetrakis(pyrid-4-yl)cyclobutane) was carried out in a single-crystal-to-single-crystal manner. The reaction product was characterized by means of X-ray diffraction and 1H NMR spectroscopy. Only the rctt-isomer of tpcb was found as the reaction product. Intermolecular interactions in a single crystal of (H2bpe)(NO3)2 were studied within the QTAIM approach. Although sum energy of strong and weak hydrogen bonds dominates in total packing energy, contribution

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5

Kole, Goutam Kumar, Geok Kheng Tan, and Jagadese J. Vittal. "Crystal engineering studies on the salts of trans-4,4′-stilbenedicarboxylic acid in the context of solid state [2 + 2] cycloaddition reaction." CrystEngComm 13, no. 9 (2011): 3138–45. http://dx.doi.org/10.1039/c0ce00224k.

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6

Altowyan, Mezna Saleh, Saied M. Soliman, Matti Haukka, Nora H. Al-Shaalan, Aminah A. Alkharboush, and Assem Barakat. "Synthesis of Unexpected Dimethyl 2-(4-Chlorophenyl)-2,3-dihydropyrrolo[2,1-a]isoquinoline-1,3-dicarboxylate via Hydrolysis/Cycloaddition/Elimination Cascades: Single Crystal X-ray and Chemical Structure Insights." Crystals 12, no. 1 (2021): 6. http://dx.doi.org/10.3390/cryst12010006.

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Hydrolysis/[3 + 2] cycloaddition/elimination cascades employed for the synthesis of unexpected tricyclic compound derived from isoquinoline. Reaction of ethylene derivative 1 with the isoquinoline ester iminium ion 2 in alkaline medium (MeOH/NEt3) under reflux for 1 h resulted in the formation of the fused pyrrolo[2,1-a]isoquinoline derivative 3. Its structure was elucidated by X-ray single crystal and other spectrophotometric tools. Hirshfeld calculations for 3 and its crystal structure analysis revealed the importance of the short O…H (19.1%) contacts and the relatively long H…C (17.1%), Cl…

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Altowyan, Mezna Saleh, Saied M. Soliman, Matti Haukka, Nora Hamad Al-Shaalan, Aminah A. Alkharboush, and Assem Barakat. "[3+2] Cycloaddition Reaction for the Stereoselective Synthesis of a New Spirooxindole Compound Grafted Imidazo[2,1-b]thiazole Scaffold: Crystal Structure and Computational Study." Crystals 12, no. 1 (2021): 5. http://dx.doi.org/10.3390/cryst12010005.

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A new spirooxindole hybrid engrafted imidazo[2,1-b]thiazole core structure was designed and achieved via [3+2] cycloaddition reaction approach. One multi-component reaction between the ethylene derivative based imidazo[2,1-b]thiazole scaffold with 6-Cl-isatin and the secondary amine under heat conditions afforded the desired compound in a stereoselective manner. The relative absolute configuration was assigned based on single-crystal X-ray diffraction analysis. Hirshfeld calculations for 4 revealed the importance of the H…H (36.8%), H…C (22.9%), Cl…H (10.4%) and S…H (6.6%), as well as the O…H

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8

Chi, Changbiao, Zhengdong Wang, Tan Liu, et al. "Crystal Structures of Fsa2 and Phm7 Catalyzing [4 + 2] Cycloaddition Reactions with Reverse Stereoselectivities in Equisetin and Phomasetin Biosynthesis." ACS Omega 6, no. 19 (2021): 12913–22. http://dx.doi.org/10.1021/acsomega.1c01593.

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9

Jagadeeswararao, Metikoti, Raquel E. Galian, and Julia Pérez-Prieto. "Photocatalysis Based on Metal Halide Perovskites for Organic Chemical Transformations." Nanomaterials 14, no. 1 (2023): 94. http://dx.doi.org/10.3390/nano14010094.

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Heterogeneous photocatalysts incorporating metal halide perovskites (MHPs) have garnered significant attention due to their remarkable attributes: strong visible-light absorption, tuneable band energy levels, rapid charge transfer, and defect tolerance. Additionally, the promising optical and electronic properties of MHP nanocrystals can be harnessed for photocatalytic applications through controlled crystal structure engineering, involving composition tuning via metal ion and halide ion variations, dimensional tuning, and surface chemistry modifications. Combination of perovskites with other

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10

Miyazawa, K., Y. Kuwasaki, A. Obayashi, and M. Kuwabara. "C60 Nanowhiskers Formed by the Liquid–liquid Interfacial Precipitation Method." Journal of Materials Research 17, no. 1 (2002): 83–88. http://dx.doi.org/10.1557/jmr.2002.0014.

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Fine needlelike crystals of C60 have been formed by a liquid–liquid interfacial precipitation method which uses an interface of the concentrated toluene solution of C60/isopropyl alcohol. The needlelike crystals of C60 with a diameter of submicrons (“C60 nanowhiskers”) were found to be single crystalline and composed of thin slabswith a thickness of about 10 nm. The intermolecular distance of the C60 nanowhiskerswas found to be shortened along the growth axis as compared with the pristine C60crystals, indicating a formation of strong bonding between C60 molecules. TheC60 nanowhiskers are assum

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11

Grobelny, Anna L., Nigam P. Rath, and Ryan H. Groeneman. "Varying the regiochemistry from a solid-state [2+2] cycloaddition reaction within a series of mixed co-crystals based upon isosteric resorcinols." Journal of Photochemistry and Photobiology A: Chemistry 382 (September 2019): 111966. http://dx.doi.org/10.1016/j.jphotochem.2019.111966.

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12

Hong, S. H., Y. J. Hwang, S. G. Lee, and D. M. Shin. "Annihilation of Photochemical Reactivity of Photo-Alignment Layer." Journal of Nanoscience and Nanotechnology 8, no. 9 (2008): 4611–15. http://dx.doi.org/10.1166/jnn.2008.ic34.

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The gas-polymer and liquid-polymer interfacial reactions of photosensitive polyimide can annihilate photo-reactive carbon–carbon double bonds, which remain after photo-alignment process. The annihilation processes dramatically affect voltage holding ratio and reorientation of photo-active functional groups. Photochemical dimerizations were identified using UV-visible and FT-IR spectroscopy. Polyimide films containing cinnamate groups were irradiated by linear polarized ultra violet (LPUV) light. Schadt et al. claims that the photo-alignment results from the anisotropy depletion of the cinnamat

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13

Hayward, John J., Roger Gumbau-Brisa, Antonio Alberola, Caroline S. Clarke, Jeremy M. Rawson, and Melanie Pilkington. "An unusual single-crystal-to-single-crystal [2 + 2] photocyclisation reaction of a TTF-arylnitrile derivative." CrystEngComm 16, no. 31 (2014): 7268–77. http://dx.doi.org/10.1039/c4ce00346b.

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14

Zhang, Jing, Jing Li, Xin Feng та ін. "Light-controlled efficient photoluminescence based on an europium β-diketonate complex with single-crystal-to-single-crystal [2+2] cycloaddition". Chemical Communications 55, № 85 (2019): 12873–76. http://dx.doi.org/10.1039/c9cc05227e.

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15

Liu, Dong, Ni-Ya Li, and Jian-Ping Lang. "Single-crystal to single-crystal transformation of 1D coordination polymervia photochemical [2+2] cycloaddition reaction." Dalton Trans. 40, no. 10 (2011): 2170–72. http://dx.doi.org/10.1039/c0dt00931h.

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16

Ogurtsov, Vladimir A., and Oleg A. Rakitin. "New Cycloadditon Reaction of 2-Chloroprop-2-enethioamides with Dialkyl Acetylenedicarboxylates: Synthesis of Dialkyl 2-[4,5-Bis(alkoxycarbonyl)-2-(aryl{alkyl}imino)-3(2H)-thienylidene]-1,3-dithiole-4,5-dicarboxylates." Molecules 27, no. 20 (2022): 6887. http://dx.doi.org/10.3390/molecules27206887.

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The 1,3-dipolar cycloaddition of 1,2-dithiole-3-thiones with alkynes to form 1,3-dithioles is one of the most studied reactions in this class of polysulfur-containing heterocycles. Nucleophilic substitution of chlorine atoms in dimethyl 2-(1,2-dichloro-2-thioxoethylidene)-1,3-dithiole-4,5-dicarboxylate, which was obtained by addition one molecules of DMAD to 4,5-dichloro-3H-1,2-dithiole-3-thione, led to a series of 2-chloro-2-(1,3-dithiol-2-ylidene)ethanethioamides. Cycloaddition reaction of 2-chloro-2-(1,3-dithiol-2-ylidene)ethanethioamides with activated alkynes led to the unexpected formati

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17

Volodin, Alexander, Alexander Korlyukov, Anna Vologzhanina, et al. "Photoinitiated solid-state [2+2] cycloaddition reaction in [Zn2(H2O)2(2-Amal)2(bpe)] (2-Amal = 2-allylmalonate) crystal." Acta Crystallographica Section A Foundations and Advances 74, a2 (2018): e398-e398. http://dx.doi.org/10.1107/s2053273318089222.

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18

Dvoracek, Metodej, Brendan Twamley, Mathias O. Senge, and Mikhail A. Filatov. "Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye." Beilstein Journal of Organic Chemistry 21 (March 5, 2025): 500–509. https://doi.org/10.3762/bjoc.21.37.

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Bimanes, a class of molecules based on the 1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione scaffold, were first introduced by E. M. Kosower in 1978. In this study, we report the topochemical cycloaddition of diethyl 2,6-dichloro-1,7-dioxo-1H,7H-pyrazolo[1,2-a]pyrazole-3,5-dicarboxylate (Cl2B), initiated by visible light. Crystal structure analysis confirmed that the reactive double bonds are parallel and coplanar, in line with the Schmidt criteria for topochemical cycloaddition. Additionally, two other bimane derivatives with different substitution patterns were synthesized and investigated. Our findi

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19

Han, Bin, Ping Hu, Bi-Qin Wang, Carl Redshaw, and Ke-Qing Zhao. "Triphenylene discotic liquid crystal trimers synthesized by Co2(CO)8-catalyzed terminal alkyne [2 + 2 + 2] cycloaddition." Beilstein Journal of Organic Chemistry 9 (December 11, 2013): 2852–61. http://dx.doi.org/10.3762/bjoc.9.321.

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The synthesis of star-shaped discotic liquid crystal trimers using Co2(CO)8-catalyzed terminal alkyne [2 + 2 + 2] cycloaddition reaction is reported. The trimers consist of three triphenylene discotic units linked to a central 1,2,4-trisubstituted benzene ring via flexible spacers. The trimers were synthesized in the yields up to 70% by mixing the monomers with 10 mol % of Co2(CO)8 as the catalyst in refluxing 1,4-dioxane. The liquid crystalline properties were investigated by using polarizing optical microscopy (POM), differential scanning calorimetry (DSC) and X-ray diffraction (XRD). Trimer

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20

Howard, Judith A. K., Mary F. Mahon, Paul R. Raithby, and Hazel A. Sparkes. "Trans-cinnamic acid and coumarin-3-carboxylic acid: experimental charge-density studies to shed light on [2 + 2] cycloaddition reactions." Acta Crystallographica Section B Structural Science 65, no. 2 (2009): 230–37. http://dx.doi.org/10.1107/s0108768109001566.

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As part of an ongoing series of experimental charge-density investigations into the intra- and intermolecular interactions present in compounds which undergo solid-state [2 + 2] cycloaddition reactions, the charge-density analyses of trans-cinnamic acid and coumarin-3-carboxylic acid are reported. Thus, high-resolution single-crystal X-ray diffraction data were recorded at 100 K for trans-cinnamic acid (sin θ/λmax = 1.03 Å−1) and coumarin-3-carboxylic acid (sin θ/λmax = 1.19 Å−1). In addition to the anticipated O—H...O hydrogen bonds weak C—H...O interactions were identified in both structures

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21

Mir, Mohammad Hedayetullah, Lip Lin Koh, Geok Kheng Tan, and Jagadese J Vittal. "Single‐Crystal to Single‐Crystal Photochemical Structural Transformations of Interpenetrated 3 D Coordination Polymers by [2+2] Cycloaddition Reactions." Angewandte Chemie International Edition 49, no. 2 (2010): 390–93. http://dx.doi.org/10.1002/anie.200905898.

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22

Mir, Mohammad Hedayetullah, Lip Lin Koh, Geok Kheng Tan, and Jagadese J Vittal. "Single‐Crystal to Single‐Crystal Photochemical Structural Transformations of Interpenetrated 3 D Coordination Polymers by [2+2] Cycloaddition Reactions." Angewandte Chemie 122, no. 2 (2009): 400–403. http://dx.doi.org/10.1002/ange.200905898.

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23

Velasco Ximello, Manuel, Sylvain Bernès, Aarón Pérez-Benítez, et al. "Crystal structure ofr-1,c-2-dibenzoyl-t-3,t-4-bis(2-nitrophenyl)cyclobutane." Acta Crystallographica Section E Crystallographic Communications 73, no. 12 (2017): 1866–70. http://dx.doi.org/10.1107/s2056989017015936.

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The condensation reaction of acetophenone (1-phenylethan-1-one) with 2-nitrobenzaldehyde in the molten state yielded the expected chalcone, (E)-3-(2-nitrophenyl)-1-phenylprop-2-en-1-one, and, unexpectedly, the title compound, C30H22N2O6, which results from thesynhead-to-head [2 + 2] cycloaddition of the chalcone. The molecular structure of the dimer shows that the four benzene rings of the substituents are oriented in such a way that potential steric hindrance is minimized, whilst allowing some degree of intermolecular π–π interactions for crystal stabilization. In the molecule, one nitro grou

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24

Borrini, Angelo, Pietro Diviersi, Giovanni Ingrosso, Antonio Lucherini, and Giorgio Serra. "Highly active rhodium catalysts for the [2+2+2] cycloaddition of acetylenes." Journal of Molecular Catalysis 30, no. 1-2 (1985): 181–95. http://dx.doi.org/10.1016/0304-5102(85)80026-2.

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25

Volodin, Alexander D., Alexander A. Korlyukov, Ekaterina N. Zorina-Tikhonova, et al. "Diastereoselective solid-state crossed photocycloaddition of olefins in a 3D Zn(ii) coordination polymer." Chemical Communications 54, no. 98 (2018): 13861–64. http://dx.doi.org/10.1039/c8cc07734g.

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1,2-Bis(pyrid-4-yl)ethylene (red) and 2-allylmalonate (blue) undergo a photoinitiated [2+2] crossed cycloaddition reaction in a 3D coordination polymer, accompanied with significant atomic movement and crystal decomposition.

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26

Burford, Neil, Charles L. B. Macdonald, Trenton M. Parks, et al. "Preparation and structure of 2-chloro-1,3-dimethyldiaza-2-arsenane, 1,3-dimethyldiaza-2-arsenanium tetrachlorogallate, and butadiene cycloadducts of diazarsenium cations." Canadian Journal of Chemistry 74, no. 11 (1996): 2209–16. http://dx.doi.org/10.1139/v96-248.

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1,3-Dimethyldiaza-2-arsenanium tetrachlorogallate (crystal data: C5H12AsCl4GaN2, M = 386.61, orthorhombic, space group Pca21, a = 14.432(3) Å, b = 6.7580(14) Å, c = 13.905(3) Å, V = 1356.2(5) Å3) is synthesized by the routine chloride ion abstraction procedure from 2-chloro-1,3-dimethyldiaza-2-arsenane (crystal data: C5H12AsClN2, M = 210.54, monoclinic, space group P21/n, a = 7.206(1) Å, b = 9.650(1) Å, c = 13.021(2) Å, β = 99.61(2)°, V = 892.8(2) Å3). X-ray crystallographic studies of both compounds are described together with that for 2-chloro-1,3-dimethyldiaza-2-arsolidine (crystal data: C4

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27

Ogoshi, Sensuke, Haruo Ikeda, and Hideo Kurosawa. "Nickel-catalyzed [2+2+2] cycloaddition of two alkynes and an imine." Pure and Applied Chemistry 80, no. 5 (2008): 1115–25. http://dx.doi.org/10.1351/pac200880051115.

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The reaction of N-benzenesulfonylbenzaldimine with Ni(cod)2 and PCy3 gave the corresponding η2-iminenickel complex quantitatively. Diphenylacetylene reacted with the η2-iminenickel complex to generate five-membered aza-nickelacycle. Insertion of second alkynes into the five-membered aza-nickelacycle led to the formation of the corresponding seven-membered aza-nickelacycles. Heating the solution of the seven-membered aza-nickelacycles induced the reductive elimination to give 1,2-dihydropyridine. In the presence of 10 mol % of Ni(cod)2 and PMetBu2 at 100 °C, the intermolecular [2+2+2] cycloaddi

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28

Medishetty, Raghavender, Terence Teck Sheng Yap, Lip Lin Koh, and Jagadese J. Vittal. "Thermally reversible single-crystal to single-crystal transformation of mononuclear to dinuclear Zn(ii) complexes by [2+2] cycloaddition reaction." Chemical Communications 49, no. 83 (2013): 9567. http://dx.doi.org/10.1039/c3cc45706k.

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29

Li, Tian-Yuan, Yu-Ze Du, Tian-Yi Xu, Tian-Le Zhang, and Fei Tong. "Shape Dependence of Photoresponsive Molecular Crystals Composed of Naphthyl Acrylic Acid Stimulated by Solid-State [2 + 2] Photocycloaddition." Crystals 14, no. 6 (2024): 492. http://dx.doi.org/10.3390/cryst14060492.

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Photomechanical molecular crystals, actuated by solid-state photochemical reactions, manifest a spectrum of mechanical motions upon light exposure, underscoring their prospective integration into the next generation of intelligent materials and devices. Utilizing the solid-state photodimerization of naphthyl acrylic acid as a paradigm, this study delved into the interplay between crystal morphology and reaction dynamics on the photomechanical responses of molecular crystals. Distinct crystal forms—bulk, microrods, and microplates—were cultivated through tailored crystallization conditions. Whi

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Lin, Hui, Peng Yang, Tinghong Fei та Fangming Liu. "Synthesis and Crystal Structure of Novel β-Lactam Derivatives Bearing Quinoline Moiety via [2 + 2] Cycloaddition". Journal of Heterocyclic Chemistry 53, № 6 (2015): 2036–41. http://dx.doi.org/10.1002/jhet.2526.

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WANG, JING-FANG, DONG-QING WEI, CHUN-FANG WANG, et al. "A THEORETICAL STUDY ON THE MECHANISM OF 2:1 1, 3 DIPOLAR CYCLOADDITION REACTIONS." Journal of Theoretical and Computational Chemistry 06, no. 04 (2007): 861–67. http://dx.doi.org/10.1142/s0219633607003489.

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The reactions between nitrile oxides and alkenes are of considerable interest in organic synthesis as the resulting heterocycles are versatile intermediates for the synthesis of natural products and biologically active compounds. In this paper, we design a series of reactions of phosphonyl nitrile oxides with acrylonnitrile, which can give 2:1 cycloaddition products with no crystal structure released so far, and present a detailed theoretical study on the mechanism of the 2:1 1, 3-dipolar cycloaddition reaction, which has been explored with density functional theory calculations at B3LYP/6-31G

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Shibata, Takanori, Toshifumi Uchiyama, Hiroyuki Hirashima, and Kohei Endo. "Enantioselective construction of new chiral cyclic scaffolds using [2 + 2 + 2] cycloaddition." Pure and Applied Chemistry 83, no. 3 (2011): 597–605. http://dx.doi.org/10.1351/pac-con-10-09-03.

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Two types of enantioselective [2 + 2 + 2] cycloadditions of triynes using chiral rhodium catalysts are disclosed. The intramolecular reaction of ortho-aminophenol-tethered triynes provides chiral tripodal compounds. Consecutive inter- and intramolecular reactions of ortho-phenylene-tethered triynes provide chiral tetraphenylenes.

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33

Cai, Jinhui, Li-Gang Bai, Yiliang Zhang, et al. "Ni-catalyzed enantioselective [2 + 2 + 2] cycloaddition of malononitriles with alkynes." Chem 7, no. 3 (2021): 799–811. http://dx.doi.org/10.1016/j.chempr.2021.02.013.

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34

Hernández, Yaiza, Isidro Marcos, Narciso M. Garrido, Francisca Sanz, and David Diez. "Crystal structure of (2R*,3aR*)-2-phenylsulfonyl-2,3,3a,4,5,6-hexahydropyrrolo[1,2-b]isoxazole." Acta Crystallographica Section E Crystallographic Communications 73, no. 1 (2017): 85–87. http://dx.doi.org/10.1107/s2056989016019952.

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The title compound, C12H15NO3S, was prepared by 1,3-dipolar cycloaddition of 3,4-dihydro-2H-pyrrole 1-oxide and phenyl vinyl sulfone. In the molecule, both fused five-membered rings display a twisted conformation. In the crystal, C—H...O hydrogen bonds link neighbouring molecules, forming chains running parallel to thebaxis.

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Pyne, Stephen G., Javad Safaei-G., Karl Schafer, Abdollah Javidan, Brian W. Skelton, and Allan H. White. "Diastereoselective 1,3-Dipolar Cycloadditions and Michael Reactions of Azomethine Ylides to (2R)-3-Benzoyl-4-methylidene-2-phenyloxazolidin-5-one and (2S)-3-Benzoyl-2-t-butyl-4-methylideneoxazolidin-5-one." Australian Journal of Chemistry 51, no. 2 (1998): 137. http://dx.doi.org/10.1071/c97072.

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The 1,3-dipolar cycloaddition reactions of (1) and (11) with the azomethine ylides derived from N-benzylidene α-amino acid esters (2) proceed with good to high exo-diastereoselectivity giving the cycloadducts (4) and (12), respectively. The cycloaddition adducts can be converted to highly functionalised prolines (14), (15) and (17) in high enantiomeric purities. The Michael addition adducts of (1) and (11) with the azomethine ylides derived from the N-(disubstituted methylidene) α-amino acid esters (18), (19) and (33) allow for a practical synthesis of all four stereoisomers of 4-benzamidopyro

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Cheng, Xiao, Fulin Yang, Jian Zhao, et al. "Microscopic visualization and mechanism investigation of the crystal jumping behavior of a cyclic chalcone derivative." Materials Chemistry Frontiers 4, no. 2 (2020): 651–60. http://dx.doi.org/10.1039/c9qm00663j.

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A highly emissive chalcone crystal which displays fantastic photo-induced jumping behavior is designed and the microscopic dynamic process is easily visualized and captured. The motion mechanism is demonstrated to be a [2+2] cycloaddition reaction.

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37

Dumitrescu, Denisa, Sergiu Shova, Constantin Draghici, Marcel Mirel Popa, and Florea Dumitrascu. "Synthesis of 1-(2-Fluorophenyl)pyrazoles by 1,3-Dipolar Cycloaddition of the Corresponding Sydnones." Molecules 26, no. 12 (2021): 3693. http://dx.doi.org/10.3390/molecules26123693.

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3-Arylsydnones bearing fluorine and bromine atoms on the benzene ring were synthesized from N-nitroso-2-fluorophenylglycines and characterized by NMR spectroscopy. These were employed further in synthesis of the corresponding 1-(2-fluorophenyl)pyrazoles by 1,3-dipolar cycloaddition reaction with dimethyl acetylenedicarboxylate (DMAD) as activated dipolarophile. The sydnones as reaction intermediates were characterized by single crystal X-ray diffraction analysis showing interesting features such as halogen bonding as an important interaction in modeling the crystal structure.

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38

Yonezawa, Hirotaka, Shohei Tashiro, Takafumi Shiraogawa, et al. "Preferential Photoreaction in a Porous Crystal, Metal–Macrocycle Framework: PdII-Mediated Olefin Migration over [2+2] Cycloaddition." Journal of the American Chemical Society 140, no. 48 (2018): 16610–14. http://dx.doi.org/10.1021/jacs.8b08534.

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39

Bhandary, S., M. Beliš, A. M. Kaczmarek, and K. Van Hecke. "Photochemical motions in organoboron-based phosphorescent molecular crystals driven by a crystal-state [2+2] cycloaddition reaction." Acta Crystallographica Section A Foundations and Advances 79, a2 (2023): C660. http://dx.doi.org/10.1107/s205327332308957x.

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40

Laus, Gerhard, Mirco E. Kostner, Volker Kahlenberg, and Herwig Schottenberger. "Synthesis and reactions of 2-azido-1,3-di(benzyloxy)imidazolium hexafluoridophosphate." Zeitschrift für Naturforschung B 71, no. 9 (2016): 997–1003. http://dx.doi.org/10.1515/znb-2016-0104.

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Abstract2-Azido-1,3-di(benzyloxy)imidazolium hexafluoridophosphate was obtained from the corresponding 2-bromo compound by reaction with sodium azide. Cycloaddition of the 2-azido compound with norbornene and norbornadiene gave the respective tricyclic aziridine and bicyclic azaoctadiene. Addition of triphenylphosphane yielded the phosphazide which upon heating eliminated dinitrogen to afford the phosphazene. The crystal structures of five compounds were determined by X-ray diffraction.

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41

Zhang, Kan, Yuefeng Bai, Chun Feng, et al. "Synthesis and characterization of new H-shaped triphenylene discotic room-temperature liquid crystal tetramers by a copper-free click reaction." New Journal of Chemistry 42, no. 1 (2018): 272–80. http://dx.doi.org/10.1039/c7nj02695a.

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42

Vollbrecht, Susanne, Uwe Klingebiel, and Dieter Schmidt-Bäse. "Additionen an die Si=N-Doppelbindung – Kristallstruktur eines (SiNCO)-Vierringes / Additions to the Si=N-Double Bond - Crystal Structure of a (SiNCO)-Four Membered Ring." Zeitschrift für Naturforschung B 46, no. 6 (1991): 709–13. http://dx.doi.org/10.1515/znb-1991-0603.

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In the reaction with benzophenone and phenylaldehyde lithiated aminofluorosilanes behave like iminosilanes. Four membered rings are formed in (2+2) cycloadditions. The oxaazasilacyclobutane ((CMe3)2Si—NCMe3—C6H5CH—O—) was purified by destillation. Single crystals were obtained by recrystallization from hexane. The thermal cleavage of the (SiNCO)-rings leads to carboimines and cyclosiloxanes. The lithium derivate of di-tert-butylfluorosilyl-2.6-diisopropylphenylamine reacts with 2-methyl-propenal-2 in two competing ways. In a (2+4) cycloaddition an 1-oxa-3-aza-2-sila-5-cyclohexene is formed, an

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43

Kvyatkovskaya, Elisaveta A., Vladimir P. Zaytsev, Fedor I. Zubkov, Pavel V. Dorovatovskii, Yan V. Zubavichus, and Victor N. Khrustalev. "Interaction between maleic acid andN-R-furfurylamines: crystal structure of 2-methyl-N-[(5-phenylfuran-2-yl)methyl]propan-2-aminium (2Z)-3-carboxyacrylate andN-[(5-iodofuran-2-yl)methyl]-2-methylpropan-2-aminium (2Z)-3-carboxyprop-2-enoate." Acta Crystallographica Section E Crystallographic Communications 73, no. 4 (2017): 515–19. http://dx.doi.org/10.1107/s2056989017003541.

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The title molecular salts, C15H20NO+·C4H3O4−, (I), and C9H15INO+·C4H3O4−, (II), have very similar molecular geometries for both cation and anion. The anions of both (I) and (II) are practically planar (r.m.s. deviations = 0.062 and 0.072 Å, respectively) and adopt a rare symmetrical geometry with the hydroxy H atom approximately equidistant from the two O atoms. In their crystals, the cations and anions in both (I) and (II) form tight ionic pairsviastrong N—H...O hydrogen bonds, with a roughly perpendicular disposition of the anion to the furan ring of the cation. This ion-pair conformation ap

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Kansui, H. "Liquid Crystal Control. Highly Diastereoselective [3+2] Nitrone-Olefin Cycloaddition in Smectic Solvent." Tetrahedron Letters 36, no. 33 (1995): 5899–902. http://dx.doi.org/10.1016/00404-0399(50)11366-.

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45

Hutchins, Kristin M., Daniel K. Unruh, and Ryan H. Groeneman. "Covalent bond formation via a [2+2] cycloaddition reaction as a tool to alter thermal expansion parameters of organic co-crystals." New Journal of Chemistry 42, no. 20 (2018): 16460–63. http://dx.doi.org/10.1039/c8nj03815e.

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46

Gill, Melvyn, Peter M. Morgan, Jin Yu, and Jonathan M. White. "Pigments of Fungi. XLVII. Cardinalic Acid, a New Anthraquinone Carboxylic Acid from the New Zealand Toadstool Dermocybe cardinalis and the Synthesis and X-Ray Crystal Structure of Methyl 1,7,8-Tri-O-methylcardinalate." Australian Journal of Chemistry 51, no. 3 (1998): 213. http://dx.doi.org/10.1071/c97154.

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Cardinalic acid (1,7,8-trihydroxy-6-methoxy-3-methyl-9,10-dioxoanthracene-2-carboxylic acid) (4) and the known anthraquinone carboxylic acids endocrocin (1), dermolutein (2) and cinnalutein (3) have been isolated from the New Zealand toadstool Dermocybe cardinalis. Methyl 1,7,8-tri-O-methylcardinalate (5) has been prepared both by permethylation of the natural product (4) and from 2,6-dichloro-1,4-benzoquinone by two consecutive regioselective Diels–Alder cycloaddition reactions. A single-crystal X-ray structure analysis of the ester (5) corroborates the structure of the natural product (4) an

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Anand, Amit, Prabhpreet Singh, Vipan Kumar, and Gaurav Bhargava. "Transition metal catalyzed [6 + 2] cycloadditions." RSC Advances 9, no. 44 (2019): 25554–68. http://dx.doi.org/10.1039/c9ra02839k.

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48

Belguedj, Roumaissa, Sofiane Bouacida, Hocine Merazig, Ali Belfaitah, Aissa Chibani, and Abdelmalek Bouraiou. "Synthesis and crystal structures of three novel benzimidazole/benzoindolizine hybrids." Zeitschrift für Naturforschung B 71, no. 3 (2016): 231–39. http://dx.doi.org/10.1515/znb-2015-0164.

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AbstractThree benzoindolizine derivatives, 1, 2, and 3, were obtained via 1,3-dipolar cycloaddition. The reaction of 1-(2′-benzimidazolylmethyl)isoquinolinium ylides with dimethyl acetylenedicarboxylate gave a mixture of pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate (1) and 1,10b-dihydropyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate (2) derivatives containing a benzimidazole moiety. The reaction of this isoquinolinium N-ylide with dimethyl maleate gave an unexpected 2,3-dihydropyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate (3). The structures of all reported compounds have been examined by X-ray cr

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Cameron, T. Stanley, Andreas Decken, Mary Gabriel, Carsten Knapp, and Jack Passmore. "Investigations of the mono- and dicycloaddition reactions of [SNS][MF6] (M = As, Sb) with the dinitriles NCC(O)CN and NCC(Cl)2CN — Energetics and the preference for [SNS]+ dicycloaddition products in solution and solid state." Canadian Journal of Chemistry 85, no. 2 (2007): 96–104. http://dx.doi.org/10.1139/v06-190.

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The stepwise symmetry-allowed cycloaddition reactions of [SNS]+ with the dinitriles NC–X–CN (X = CCl2, CO) were investigated. The reaction of [SNS]+ and dinitrile in 2:1 ratio yielded the dicycloaddition product quantitatively after 2 weeks (in situ 13C NMR). At a 1:1 ratio, mixtures of mono- and dicycloaddition products were obtained that could not be completely separated from one another. The energetics of the reaction were estimated in the gas phase, in solution (SO2 and CH2Cl2), and solid phases using DFT calculations (PBE0/6-311G*) and a "volume-based thermodynamics" approach for lattice

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50

Wang, Kai-Kai, Yan-Li Li, Ming-Yue Wang, Jun Jing, Zhan-Yong Wang, and Rongxiang Chen. "[3 + 2] cycloaddition of nonstabilized azomethine ylides and 2-benzothiazolamines to access imidazolidine derivatives." RSC Advances 12, no. 44 (2022): 28295–98. http://dx.doi.org/10.1039/d2ra04616d.

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An effective method for the synthesis of functionalized imidazolidine derivatives via a [3 + 2] cycloaddition reaction from nonstabilized azomethine ylides generated in situ from 2-benzothiazolamines in high yields (up to 98%) has been developed.

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