RSS-Feed abonnieren
PDF herunterladen
DOI: 10.1055/a-2655-3036
Tetraethynylmethane: A Quest for the “Dutch Diamond”
Authors
Part of this research was supported by an FSE Research Grant (2022-04) by the University of Groningen.
Abstract
Tetraethynylmethane is an elusive building block that has motivated generations of organic chemists to provide an efficient synthesis. Despite being thermally unstable, several reports have culminated in its effective synthesis, and initial applications as porous material were described. However, the uniqueness of this molecule has not reached its full potential, both from a synthetic and applied point of view.
Publikationsverlauf
Eingereicht: 08. Juni 2025
Angenommen nach Revision: 14. Juli 2025
Accepted Manuscript online:
14. Juli 2025
Artikel online veröffentlicht:
04. September 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1 Hirsch A. Nat Mater 2010; 9: 868-871
- 2 Diederich F, Rubin Y. Angew Chem Int Ed Engl 1992; 31: 1101-1123
- 3 Chen L, Huo J, Zhang J. et al. Green synth Catal 2023; 4: 273-292
- 4 Berger JG, Stogryn EL, Zimmerman AA. J Org Chem 1964; 29: 950-951
- 5 Alberts AH. In Lemstra PJ, Kleintjens LA. eds Integration of Fundamental Polymer Science and Technology—4. Dordrecht, Netherlands: Springer; 1990: 396-401
- 6a Alberts AH, Wynberg H, Chem J. Soc, Chem Commun 1988; 748-749
- 6b Alberts AH. J Am Chem Soc 1989; 111: 3093-3094
- 7 Bunz U, Vollhardt KPC, Ho JS. Angew Chem Int Ed Engl 1992; 31: 1648-1651
- 8 Chauvin R. Tetrahedron Lett 1995; 36: 397-400
- 9 Feldman KS, Kraebel CM, Parvez M. J Am Chem Soc 1993; 115: 3846-3847
- 10 Ma B, Sulzbach HM, Xie Y, Schaefer III HF. J Am Chem Soc 1994; 116: 3529-3538
- 11 Capitani JF. J Mol Struct (THEOCHEM) 1995; 332: 21-23
- 12 Tatevosyan MM, Zhukova TN, Vlasenko VG. J Struct Chem 2021; 62: 1684-1693
- 13 Rayne S, Forest K. Comput Theor Chem 2011; 970: 15-22
- 14 Raynor S, Song HH. ACS Omega 2020; 5: 27546-27555
- 15 Sjövall P, Bake KD, Pomerantz AE, Lu X, Mitra-Kirtley S, Mullins OC. Fuel 2021; 286: 119373
- 16a Müller E, Segnitz A. Liebigs Ann Chem 1973; 1973: 1583-1591
- 16b Hauptmann H. Tetrahedron 1976; 32: 1293-1297
- 16c Posner GH, Loomis GL, Sawaya HS. Tetrahedron Lett 1975; 16: 1373-1376
- 17 Feldman KS, Weinreb CK, Youngs WJ, Bradshaw JD. J Am Chem Soc 1994; 116: 9019-9026
- 18 Feldman KS, Weinreb CK, Youngs WJ, Bradshaw JD. J Org Chem 1994; 59: 1213-1215
- 19 Amemiya R, Suwa K, Toriyama J, Nishimura Y, Yamaguchi M. J Am Chem Soc 2005; 127: 8252-8253
- 20 Amemiya R, Yamaguchi M. Adv Synth Catal 2007; 349: 1011-1014
- 21 Zhao Z, Das S, Xing G. et al. Angew Chem Int Ed 2018; 57: 11952-11956
- 22 Feldman KS, Mareska DA, Weinreb CK, Chasmawala M. Chem Commun 1996; 865-866
- 23 Huang CY, Song Y. CN108892119 2018
- 24 Heasman P, Varley E, Trewin A. Energy Fuel 2022; 36: 6560-6568
- 25 Wang J, Fu X, Yan N, Zhang Y. ChemSusChem 2021; 14: 3806-3809