ドデカヘドラン
ドデカヘドラン
出典: フリー百科事典『ウィキペディア（Wikipedia）』 (2023/04/21 08:49 UTC 版)
ドデカヘドラン（dodecahedrane、化学式: C20H20）は、有機化合物の1つで、1982年にオハイオ州立大学のレオ・パケットにより、主に「十二面体の対称性を審美的に探求した」結果として初めて合成された[2][3]。
- ^ a b Bertau, Martin; Wahl, Fabian; Weiler, Andreas; Scheumann, Klaus; Wörth, Jürgen; Keller, Manfred; Prinzbach, Horst (1997). “From Pagodanes to Dodecahedranes - Search for a Serviceable Access to the Parent (C20H20) Hydrocarbon”. Tetrahedron 53 (29): 10029–10040. doi:10.1016/S0040-4020(97)00345-1. ISSN 0040-4020.
- ^ Ternansky, Robert J.; Balogh, Douglas W.; Paquette, Leo A. (1982). “Dodecahedrane”. Journal of the American Chemical Society 104 (16): 4503–4504. doi:10.1021/ja00380a040.
- ^ a b Leo A. Paquette, Robert J. Ternansky, Douglas W. Balogh, and Gary Kentgen (1983). “Total synthesis of dodecahedrane”. Journal of the American Chemical Society 105 (16): 5446–5450. doi:10.1021/ja00354a043.
- ^ IUPAC name: hexadecahydro-5,2,1,6,3,4-[2,3]butanediyl[1,4]diylidenedipentaleno[2,1,6-cde:2',1',6'-gha]pentalene CAS number: 4493-23-6
- ^ Eaton, Philip E. (1979). “Towards dodecahedrane”. Tetrahedron 35 (19): 2189–2223. doi:10.1016/0040-4020(79)80114-3. ISSN 0040-4020.
- ^ Leo A. Paquette, Douglas W. Baloghr (1983). “An expedient synthesis of 1,16-dimethyldodecahedrane”. Journal of the American Chemical Society 104 (3): 774–783. doi:10.1021/ja00367a021.
- ^ Paquette, Leo A.; Wyvratt, Matthew J. (1974). “Domino Diels-Alder reactions. I. Applications to the rapid construction of polyfused cyclopentanoid systems”. Journal of the American Chemical Society 96 (14): 4671–4673. doi:10.1021/ja00821a052.
- ^ Paquette, Leo A.; Wyvratt, Matthew J.; Schallner, Otto; Muthard, Jean L.; Begley, William J.; Blankenship, Robert M.; Balogh, Douglas (1979). “Topologically spherical molecules. Synthesis of a pair of C2-symmetric hexaquinane dilactones and insights into their chemical reactivity. An efficient .pi.-mediated 1,6-dicarbonyl reduction”. The Journal of Organic Chemistry 44 (21): 3616–3630. doi:10.1021/jo01335a003.
- ^ Fessner, Wolf-Dieter; Murty, Bulusu A. R. C.; Prinzbach, Horst (1987). “The Pagodane Route to Dodecahedranes—Thermal, Reductive, and Oxidative Transformations of Pagodanes”. Angewandte Chemie International Edition in English 26 (5): 451–452. doi:10.1002/anie.198704511. ISSN 1521-3773.
- ^ Fessner, Wolf-Dieter; Murty, Bulusu A. R. C.; Wörth, Jürgen; Hunkler, Dieter; Fritz, Hans; Prinzbach, Horst; Roth, Wolfgang D.; Schleyer, Paul von Ragué et al. (1987). “Dodecahedranes from [1.1.1.1Pagodanes”]. Angewandte Chemie International Edition in English 26 (5): 452–454. doi:10.1002/anie.198704521. ISSN 1521-3773.
- ^ Prakash, G. K. Surya.; Krishnamurthy, V. V.; Herges, Rainer.; Bau, Robert.; Yuan, Hanna.; Olah, George A.; Fessner, Wolf Dieter.; Prinzbach, Horst. (1988). “Stable carbocations. 273. [1.1.1.1- and [2.2.1.1]Pagodane dications: frozen two-electron Woodward-Hoffmann transition-state models”]. Journal of the American Chemical Society 110 (23): 7764–7772. doi:10.1021/ja00231a029.
- ^ Prinzbach, Horst; Weiler, Andreas; Landenberger, Peter; Wahl, Fabian; Worth, Jurgen; Scott, Lawrence T.; Gelmont, Marc; Olevano, Daniela et al. (2000年9月7日). “Gas-phase production and photoelectron spectroscopy of the smallest fullerene, C20”. Nature 407 (6800): 60–63. doi:10.1038/35024037. ISSN 0028-0836.
- ^ Prinzbach, Horst; Wahl, Fabian; Weiler, Andreas; Landenberger, Peter; Wörth, Jürgen; Scott, Lawrence T.; Gelmont, Marc; Olevano, Daniela et al. (2006). “C20 Carbon Clusters: Fullerene–Boat–Sheet Generation, Mass Selection, Photoelectron Characterization”. Chemistry – A European Journal 12 (24): 6268–6280. doi:10.1002/chem.200501611. ISSN 1521-3765.
- ^ Cross, R. James; Saunders, Martin; prinzbach, Horst (1999). “Putting Helium Inside Dodecahedrane”. Organic Letters 1 (9): 1479–1481. doi:10.1021/ol991037v.
- ^ 佐藤健太郎 (2012年11月6日). “世界最小のヘリウム風船”. 2016年2月21日閲覧。
- ^ a b Wahl, Fabian; Weiler, Andreas; Landenberger, Peter; Sackers, Emmerich; Voss, Torsten; Haas, Alois; Lieb, Max; Hunkler, Dieter et al. (2006). “Towards Perfunctionalized Dodecahedranes—En Route to C20 Fullerene”. Chemistry – A European Journal 12 (24): 6255–6267. doi:10.1002/chem.200501618. ISSN 1521-3765.
- ^ Siadati, Seyyed Amir; Mirabi, Ali (2013). “A DFT study on the functionalization of C20 Fullerene via its 1,3 -dipolar cycloaddition with 4 - pyridine nitrile oxide”. IranJOC 5: 1099–1102.
- ^ Siadati, Seyyed Amir; Alinezhad, Miaad (2015). “A theoretical study on the functionalisation process of C18NB fullerene through its open [5,5 cycloaddition with 4-pyridine nitrile oxide”]. Progress in Reaction Kinetics and Mechanism 40: 169–176. doi:10.3184/146867815X14262612008408.
- ^ Siadati, Seyyed Amir (2016). “A Theoretical Study on the Possibility of Functionalization of C20 Fullerene Via its Diels-Alder Reaction with 1,3-Butadiene”. Letters in Organic Chemistry 13: 2–6. doi:10.2174/1570178612666151002002526.
- ^ Siadati, Seyyed Amir; Mirabi, Ali (2015). “Diels–Alder versus 1,3-dipolar cycloaddition pathways in the reaction of C20 fullerene and 2-furan nitrile oxide”. Progress in Reaction Kinetics and Mechanism 40: 383-390. doi:10.3184/146867815X14413752286065.
[続きの解説]
「ドデカヘドラン」の続きの解説一覧
- 1 ドデカヘドランとは
- 2 ドデカヘドランの概要
- 3 誘導体
- ドデカヘドランのページへのリンク
