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Showing posts with label Cookson’s Dione. Show all posts
Showing posts with label Cookson’s Dione. Show all posts

Tuesday, 17 April 2018

Cookson’s Dione

Chemical Names:Cyclopentadienebenzoquinone; 1200-89-1; 1,4,4a,8a-Tetrahydro-1,4-methanonaphthalene-5,8-dione; 1,4-Methanonaphthalene-5,8-dione, 1,4,4a,8a-tetrahydro-; NSC 25329; 1,4,4a,8a-Tetrahydro-endo-1,4-methanonaphthalene-5,8-dione
Molecular Formula:C11H10O2
Molecular Weight:174.199 g/mol
1H NMR (CDCl3, 400 MHz) δ = 1.41 (dt, J = 8.8, 1.5 Hz, 1H), 1.52 (dt, J = 8.8, 1.8 Hz, 1H), 3.20 (dd, J = 2.5, 1.5 Hz, 2H), 3.52 (m, 2H), 6.04 (t, J = 1.9 Hz, 2H), 6.54 (s, 2H).
13C NMR (CDCl3, 100 MHz) δ = 48.4 (2 × CH), 48.8 (CH), 48.9 (2 × CH), 135.4 (2 × CH), 142.1 (2 × CH), 199.5 (2 × CO)
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.8b00037
Abstract ImageWe report the use of a simple rotary evaporator as a semi-continuous UV photochemical reactor. By generation of a thin film from the rotation of a flask, better light penetration is achieved, and in this work we used high-power Hg lamps to enable the direct irradiation of molecules with UV light. The intramolecular [2 + 2] photocycloaddition of Cookson’s dione and the intermolecular [2 + 2] photocycloaddition of maleimide with 1-hexyne were used as test reactions to examine the effectiveness of this reactor. High productivities, equivalent to 210 g h–1, were obtained for the simple intramolecular reaction, demonstrating the scalability of the reactor. The effects of flask size, reaction mixture volume, and use of borosilicate or quartz glassware were also investigated.

Cookson’s Dione

CAS No.: 2958-72-7
1H NMR (CDCl3, 300 MHz) δ = 1.86 (d, J = 11.3, 1H), 2.02 (d, J = 11.3, 1H), 2.68 (m, 2H), 2.79 (m, 2H), 2.90 (m, 2H), 3.15 (m, 2H).
References 1. Clark, C. A.; Lee, D. S.; Pickering, S. J.; Poliakoff, M.; George, M. W. Org. Process Res. Dev. 2016, 20, 1792-1798. 2. Elliott, L. D.; Knowles, J. P.; Koovits, P. J.; Maskill, K. G.; Ralph, M. J.; Lejeune, G.; Edwards, L. J.; Robinson, R. I.; Clemens, I. R.; Cox, B.; Pascoe, D. D.; Koch, G.; Eberle, M.; Berry, M. B.; Booker-Milburn, K. I. Chem. Eur. J. 2014, 20, 15226-15232. 3. Marchand, A. P.; Allen, R. W. J. Org. Chem. 1974, 39, 1596-1596. 4. Elliott, L. D.; Berry, M.; Harji, B.; Klauber, D.; Leonard, J.; Booker-Milburn, K. I. Org. Process Res. Dev. 2016, 20, 1806-1811. 5. Hook, B. D. A.; Dohle, W.; Hirst, P. R.; Pickworth, M.; Berry, M. B.; Booker-Milburn, K. I. J Org Chem 2005, 70, 7558-7564.


Oct 3, 2016 - Cookson's Dione 125 W Batch Reaction A solution of Diels Alder adduct 3[3] (2.61 g, 15 mmol) in degassed EtOAc (150 ml) was irradiated with a pre-warmed 125 W medium pressure mercury lamp in a 150 ml batch reactor equipped with a. Pyrex immersion well for 15 min. The solvent was removed in ..

Monday, 3 October 2016

Cookson’s Dione

Cookson’s Dione

125 W Batch Reaction
A solution of Diels Alder adduct 3[3] (2.61 g, 15 mmol) in degassed EtOAc (150 ml) was irradiated with a pre-warmed 125 W medium pressure mercury lamp in a 150 ml batch reactor equipped with a
Pyrex immersion well for 15 min. The solvent was removed in vacuo and chromatography on silica
(40% EtOAc in hexane to 100% EtOAc) yielded Cookson’s dione 4 as an off-white solid (2.38 g, 91%)

1.5 kW Flow Reaction
A solution of Diels Alder adduct 3 (436 g, 2.5 mol) in degassed EtOAc (0.5 M) was irradiated with the firefly reactor fitted with a Pyrex inner filter and lamp at 1.5 kW at 36 ml/min. The mixture was
concentrated in vacuo to a slurry to which was added hexane. The mixture was filtered, washing
with petroleum ether and the solid dried to give pure Cookson’s dione 4 as an off-white crystalline
solid (387 g, 89%): m.p. 242 - 243°C;

δH (400 MHz, CDCl3) 3.19 – 3.14 (2H, m, 2×CH), 2.95 – 2.90 (2H,m, 2×CH), 2.82 – 2.78 (2H, m, 2×CH), 2.72 – 2.68 (2H, m, 2×CH), 2.04 (1H, app. d, J = 11.4 Hz, CHH),
1.88 (1H, app. d, J = 11.4 Hz, CHH);

 δC (100 MHz, CDCl3) 212. 2 (2×C), 54.9 (2×CH), 44.8 (2×CH), 43.9 (2×CH), 40.6 (CH2), 38.9 (2×CH)

SMILES O=C2[C@@H]1[C@@H]3C[C@@H]4[C@H]1C(=O)[C@H]5[C@H]2[C@H]3[C@H]45

Palladium(0)-Catalyzed Methylcyclopropanation of Norbornenes with Vinyl Bromides and Mechanism Study

 Department of Chemistry, Zhejiang University, Hangzhou 310028, Zhejiang, P.R. China
 School of Metallurgy and Chemical Engineering, Jiangxi University of Science and Technology, Ganzhou 341000, Jiangxi, P.R. China
§ School of Food Science and Biotechnology, Zhejiang Gongshang University, Hangzhou 310035, Zhejiang P.R. China
Org. Lett.201517 (15), pp 3678–3681
DOI: 10.1021/acs.orglett.5b01603
*E-mail: wlbao@zju.edu.cn.


Abstract Image
An unusual methylcyclopropanation from [2 + 1] cycloadditions of vinyl bromides to norbornenes catalyzed by Pd(OAc)2/PPh3 in the presence of CH3ONa and CH3OH has been established. A methylcyclopropane subunit was installed by a 3-fold domino procedure involving a key protonation course. Preliminary deuterium-labeling studies revealed that the proton came from methyl of CH3OH and also exposed an additional hydrogen/deuterium exchange process. These two proton-concerned reactions were fully chemoselective.


J. Mao, H. Xie, W. Bao, Org. Lett. 2015, 17, 3678 – 3681


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Molecules 200712(2), 271-282; doi:10.3390/12020271
Full Paper
Synthesis and Biological Evaluation of Rigid Polycyclic Derivatives of the Diels-Alder Adduct Tricyclo[,7]undeca-4,9-dien-3,6-dione
Felicia Megumi Ito 1, Jacqueline Marques Petroni 1, Dênis Pires de Lima 1, Adilson Beatriz 1,*, Maria Rita Marques 2, Manoel Odorico de Moraes 3, Letícia Veras Costa-Lotufo 3, Raquel  Carvalho Montenegro 3, Hemerson Iury Ferreira Magalhães 3 and Cláudia do Ó Pessoa 3
Department of Chemistry, Federal University of Mato Grosso do Sul, Campo Grande, 
MS, Brazil,,
Department of Morphophysiology, Federal University of Mato Grosso do Sul, 
Campo Grande, MS, Brazil
Department of Physiology and Pharmacology, Federal University of Ceará, 
Fortaleza, CE, Brazil,,,
Author to whom correspondence should be addressed;
  1. Cookson, R.C.; Grundwell, E.; Hudec, J. Synthesis of cage-like molecules 
  2. by irradiation of Diels-Alder adducts. Chem. Ind. (London) 1958, 1003–1004. [Google Scholar]