First example of ring carbomer of 1,4-cyclohexadiene
DOI:
https://doi.org/10.17721/fujcV3I1P60-65Keywords:
butatrienes, carbo-cyclohexadienes, carbo-mers, nucleophilic trifluoromethylationAbstract
While a series of carbo-mers of 1,3-cyclohexadienes was reported through the use of a specifically developed synthetic strategy, no example of their 1,4-regioisomers was known. Inspired by the methodology elaborated for the preparation of the 1,3-isomers, the synthesis of the first example of carbo-mer of 1,4-cyclohexadiene is presented. Comparison of physico-chemical properties of this first representative with those of the recently described 1,4-regioisomer, especially UV-vis absorption properties, is also addressed.
References
Leroyer L, Lepetit C, Rives A, Maraval V, Saffon-Merceron N, Kandaskalov D, Kieffer D, Chauvin R. From Hexaoxy-[6]Pericyclynes to Carbo -Cyclohexadienes, Carbo -Benzenes, and Dihydro- Carbo -Benzenes: Synthesis, Structure, and Chromophoric and Redox Properties . Chemistry - A European Journal 2012;18(11):3226-3240. https://doi.org/10.1002/chem.201102993
Chauvin R. “Carbomers”. I. A general concept of expanded molecules. Tetrahedron Letters 1995;36(3):397-400. https://doi.org/10.1016/0040-4039(94)02275-g
Maraval V, Chauvin R. From Macrocyclic Oligo-acetylenes to Aromatic Ring Carbo -mers . Chemical Reviews 2006;106(12):5317-5343. https://doi.org/10.1021/cr050964e
Scott L, DeCicco G, Hyun J, Reinhardt G. Decamethyl[5]pericyclyne. A novel homoconjugated cyclic polyacetylene. J. Am. Chem. Soc. 1983;105(26):7760-7761. https://doi.org/10.1021/ja00364a057
Scott L, DeCicco G, Hyun J, Reinhardt G. Cyclynes. Part 4. Pericyclynes of the order [5], [6], [7], and [8]. Simple convergent syntheses and chemical reactions of the first homoconjugated cyclic polyacetylenes. J. Am. Chem. Soc. 1985;107(23):6546-6555. https://doi.org/10.1021/ja00309a021
Maurette L, Tedeschi C, Sermot E, Soleilhavoup M, Hussain F, Donnadieu B, Chauvin R. Synthesis and stereochemical resolution of functional [5]pericyclynes. Tetrahedron 2004;60(44):10077-10098. https://doi.org/10.1016/j.tet.2004.07.052
Saccavini C, Tedeschi C, Maurette L, Sui-Seng C, Zou C, Soleilhavoup M, Vendier L, Chauvin R. Functional [6]Pericyclynes: Synthesis through [14+4] and [8+10] Cyclization Strategies. Chemistry - A European Journal 2007;13(17):4895-4913. https://doi.org/10.1002/chem.200601191
Leroyer L, Zou C, Maraval V, Chauvin R. Synthesis and stereochemical resolution of a [6]pericyclynedione: Versatile access to pericyclynediol precursors of carbo-benzenes. Comptes Rendus Chimie 2009;12(3-4):412-429. https://doi.org/10.1016/j.crci.2008.09.018
Kuwatani Y, Watanabe N, Ueda I. Synthesis of the first 3,6,9,15,18,18-hexa-substituted-1,2,4,5,7,8,10,11,13,14,16,17-dodecadehydro[18]annulenes with D6h-symmetry. Tetrahedron Letters 1995;36(1):119-122. https://doi.org/10.1016/0040-4039(94)02181-a
Suzuki R, Tsukuda H, Watanabe N, Kuwatani Y, Ueda I. Synthesis, structure and properties of 3,9,15-tri- and 3,6,9,12,15,18-hexasubstituted dodecadehydro[18]annulenes (C18H3R3 and C18R6) with D6h-symmetry. Tetrahedron 1998;54(11):2477-2496. https://doi.org/10.1016/s0040-4020(98)00011-8
Chauvin R. “Carbomers”. II. En route to [C,C]6carbo-benzene. Tetrahedron Letters 1995;36(3):401-404. https://doi.org/10.1016/0040-4039(94)02276-h
Saccavini C, Sui-Seng C, Maurette L, Lepetit C, Soula S, Zou C, Donnadieu B, Chauvin R. Functional [6]Pericyclynes: Aromatization to Substitutedcarbo-Benzenes. Chemistry - A European Journal 2007;13(17):4914-4931. https://doi.org/10.1002/chem.200601193
Zou C, Duhayon C, Maraval V, Chauvin R. Hexasilylated Total Carbomer of Benzene. Angewandte Chemie International Edition 2007;46(23):4337-4341. https://doi.org/10.1002/anie.200605262
Rives A, Baglai I, Malytskyi V, Maraval V, Saffon-Merceron N, Voitenko Z, Chauvin R. Highly π electron-rich macro-aromatics: bis(p-aminophenyl)-carbo-benzenes and their DBA acyclic references. Chemical Communications 2012;48(70):8763. https://doi.org/10.1039/c2cc34176j
Baglai I, Maraval V, Bijani C, Saffon-Merceron N, Voitenko Z, Volovenko Y, Chauvin R. Enhanced π-frustration in carbo-benzenic chromophores. Chemical Communications 2013;49(75):8374. https://doi.org/10.1039/c3cc43204a
Rives A, Baglai I, Barthes C, Maraval V, Saffon-Merceron N, Saquet A, Voitenko Z, Volovenko Y, Chauvin R. Carbo-cyclohexadienes vs. carbo-benzenes: structure and conjugative properties. Chem. Sci. 2015;6(2):1139-1149. https://doi.org/10.1039/c4sc02742f
Maraval V, Leroyer L, Harano A, Barthes C, Saquet A, Duhayon C, Shinmyozu T, Chauvin R. 1,4-Dialkynylbutatrienes: Synthesis, Stability, and Perspectives in the Chemistry of carbo-Benzenes. Chemistry - A European Journal 2011;17(18):5086-5100. https://doi.org/10.1002/chem.201002769
Cartwright H. Color perception and factor analysis. J. Chem. Educ. 1986;63(11):984. https://doi.org/10.1021/ed063p984
Kreft S, Kreft M. Physicochemical and physiological basis of dichromatic colour. Naturwissenschaften 2007;94(11):935-939. https://doi.org/10.1007/s00114-007-0272-9
van Loon J, Seiler P, Diederich F. Tetrakis(trialkylsilylethynyl)butatriene and 1,1,4,4-Tetrakis(trialkylsilylethynyl)-1,3-butadiene: Novel Cross-Conjugated Chromophores. Angewandte Chemie International Edition in English 1993;32(8):1187-1189. https://doi.org/10.1002/anie.199311871
Auffrant A, Diederich F, Boudon C, Gisselbrecht J, Gross M. Synthesis of 1,4-Diethynyl- and 1,1,4,4-Tetraethynylbutatrienes. Helvetica Chimica Acta 2004;87(12):3085-3105. https://doi.org/10.1002/hlca.200490277
Auffrant A, Jaun B, Jarowski P, Houk K, Diederich F. Peralkynylated Buta-1,2,3-Trienes: Exceptionally Low Rotational Barriers of Cumulenic C-C Bonds in the Range of Those of Peptide C-N Bonds. Chemistry - A European Journal 2004;10(12):2906-2911. https://doi.org/10.1002/chem.200400218
Leroyer L, Maraval V, Chauvin R. Synthesis of the Butatriene C 4 Function: Methodology and Applications . Chemical Reviews 2012;112(3):1310-1343. https://doi.org/10.1021/cr200239h
Singh R, Cao G, Kirchmeier R, Shreeve J. Cesium Fluoride Catalyzed Trifluoromethylation of Esters, Aldehydes, and Ketones with (Trifluoromethyl)trimethylsilane. The Journal of Organic Chemistry 1999;64(8):2873-2876. https://doi.org/10.1021/jo982494c
Simon J, Nguyen T, Chelain E, Lensen N, Pytkowicz J, Chaume G, Brigaud T. Concise synthesis of enantiopure (S)- and (R)-α-trifluoromethyl aspartic acid and α-trifluoromethyl serine from chiral trifluoromethyl oxazolidines (Fox) via a Strecker-type reaction. Tetrahedron: Asymmetry 2011;22(3):309-314. https://doi.org/10.1016/j.tetasy.2011.01.007
Simon J, Chelain E, Brigaud T. Highly Diastereoselective Synthesis of Enantiopure β-Trifluoromethyl β-Amino Alcohols from Chiral Trifluoromethyl Oxazolidines (Fox). Org. Lett. 2012;14(2):604-607. https://doi.org/10.1021/ol2032174
Fleury A, Chelain E, Brigaud T. manuscript in preparation.
Rives A, Maraval V, Saffon-Merceron N, Chauvin R. Functional carbo -Butadienes: Nonaromatic Conjugation Effects through a 14-Carbon, 24-π-Electron Backbone . Chemistry - A European Journal 2013;20(2):483-492. https://doi.org/10.1002/chem.201303169
Black K, Rives A, Barthes C, Chelain E, Brigaud T, Maraval V, Chauvin R. unpublished results
Downloads
Published
Issue
Section
License
Authors who publish with this journal agree to the following terms:
Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).