Journal of University of Chinese Academy of Sciences >
Mechanism of the condensation-rearrangement reactions of tropone with 1,2-dimethoxybenzene under the action of concentrated sulfuric acid
Received date: 2015-04-21
Revised date: 2015-05-08
Online published: 2016-01-15
The reactions of tropone (cycloheptatrienone) gave the cycloaddition products frequently, and occasionally substitutions on the olefins bonds also occurred. For 1,2-dimethoxybenzene, previous studies concerned its condensation reactions with the different aldehydes or ketones,more limited to the aryl aldehydes or saturated aliphatic aldehydes and ketones, under the action of acid.We study the condensation reaction of conjugated polyene unsaturated ketone with o-dimethoxybenzene, and the results show that not only the dehydration condensation occurs under the action of acid, but also the interesting shrink ring rearrangement reaction occurs in which a seven-membered ring converts to a six-membered aromatic ring.
ZHANG Tong , HE Wei , ZHU Zhongpeng , YANG Jingkui . Mechanism of the condensation-rearrangement reactions of tropone with 1,2-dimethoxybenzene under the action of concentrated sulfuric acid[J]. Journal of University of Chinese Academy of Sciences, 2016 , 33(1) : 65 -69 . DOI: 10.7523/j.issn.2095-6134.2016.01.010
[1] Kende A S. The course of tropone photodimerization in acetonitrile[J]. J Am Chem Soc, 1966, 88 (21): 5 026-5 027.
[2] Mukai T, Tezuka T, Akasaki Y. Tropone dimer:a new type of photocycloaddition reaction[J]. J Am Chem Soc, 1966, 88 (21): 5 025-5 026.
[3] Isakovic L, Ashenhurst J A, Gleason J L. Application of Lewis acid catalyzed tropone cycloadditions to the synthesis of the core of CP-225,917 [J]. Org Lett, 2001, 3 (26): 4 189-4 192.
[4] Du Y S, Feng J Q, Lu X Y. A phosphine-Catalyzed annulation reaction of modified allylic compounds and tropone[J]. Org Lett, 2005, 7 (10): 1 987-1 989.
[7] Williams R V, Edwards W D, Zhang P R, et al. Experimental verification of the homoaromaticity of 1,3,5-cycloheptatriene and evaluation of the aromaticity of tropone and the tropylium cation by use of the dimethyldihydropyrene probe[J]. J Am Chem Soc, 2012, 134 (40): 16 742-16 752.
[6] Rivero A R, Fernández I, Sierra M Á. Regio-and diastereo-selective stepwise -cycloaddition reaction between tropone derivatives and donor-acceptor cyclopropanes[J]. Org Lett, 2013, 15 (19): 4 928-4 931.
[7] Kumar P, Thakur A, Hong X, et al. Ni(NHC)]-catalyzed cycloaddition of ciynes and tropone: apparent enone cycloaddition involving an 8π Insertion [J]. J Am Chem Soc, 2014, 136 (51): 17 844-17 851.
[8] Davidson I M, Musgrave O C. Condensation of diketones with aromatic compounds. 2. Condensation of hexane-2,5-dione with veratrole and catechol[J]. J Chem Soc, 1963:3 154-3 155.
[9] Chung Y, Duerr B F, McKelvey T A, et al. Structural effects controlling the rate of the retro-Diels-Alder reaction in anthracene cycloadducts [J]. J Org Chem, 1989, 54: 1 018-1 032.
[10] Chopra N, Hardie M J, Raston C L. Discovery of a novel C-60 receptor based on substituted anthracene[J]. Supramolecular Chemistry, 2000, 11 (4): 275-278.
[11] Goossens R, Smet M, Dehaen W. Bronsted-and Lewis acid-catalyzed cyclization giving rise to substituted anthracenes and acridines[J]. Tetrahedron Lett, 2002, 43 (37): 6 605-6 608.
[12] Balaban T S, Eichöfer A, Krische M J, et al. Hierarchic supramolecular interactions within assemblies in solution and in the crystal of 2,3,6,7-tetrasubstituted 5,5'-(anthracene-9,10-diyl)bis homotrimer of 2,3,6,7-tetramethoxy-9,10-dimethylanthracene cation radical[J]. Tetrahedron Lett, 2009, 50: 6 687-6 690.
[16] Ogoshi T, Kitajima K, Umeda K, et al. Lewis acid-catalyzed synthesis of dodecamethoxycalix 4 arene from 1,3,5-trimethoxybenzene and its conformational behavior and host- guest property[J]. Tetrahedron, 2009, 65 (51): 10 644-10 649.
[17] Ghanem B S, Hashem M, Harris K D M, et al. Triptycene-based polymers of intrinsic microporosity: organic materials that can be tailored for gas adsorption[J]. Macromolecules, 2010, 43:5 287-5 294.
[18] Xia Z Y, Su J H, Wong W Y, et al. High performance organic light-emitting diodes based on tetra(methoxy)-containing anthracene derivatives as a hole transport and electron-blocking layer[J]. J Mater Chem, 2010, 20 (38): 8 382-8 388.
[19] Wei J, Han B, Guo Q, et al. 1,5,9-Triazacoronenes: a family of polycyclic heteroarenes synthesized by a threefold pictet-spengler reaction[J]. Angew Chem Int Ed, 2010, 49 (44): 8 209-8 213.
[20] Mohammadpoor-Baltork I, Moghadam M, Tangestaninejad S, et al. H3PW12O40-catalysed alkylation of arenes and diveratrylmethanes:convenient routes to triarylmethanes and to symmetrical and unsymmetrical 9,10-diaryl-2,3,6,7-tetramethoxyanthracenes[J]. Eur J Org Chem, 2011 (7): 1 357-1 366.
[21] Babu B M, Thakur P B, Rao N N, et al. A rapid, highly efficient, and general protocol for the synthesis of functionalized triarylmethanes: a straightforward access for the synthesis of (-)-tatarinoid C[J]. Tetrahedron Lett, 2014, 55 (11): 1 868-1 872.
/
| 〈 |
|
〉 |