First example of ring carbomer of 1,4-cyclohexadiene

Cécile Barthes; Arnaud Rives; Valérie Maraval; Evelyne Chelain; Thierry Brigaud; Remi Chauvin

doi:10.17721/fujcV3I1P60-65

Authors

Cécile Barthes CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, F-31077 Toulouse Cedex 4, France Université de Toulouse, UPS, ICT-FR 2599, 31062 Toulouse Cedex 9, France.
Arnaud Rives CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, F-31077 Toulouse Cedex 4, France Université de Toulouse, UPS, ICT-FR 2599, 31062 Toulouse Cedex 9, France.
Valérie Maraval CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, F-31077 Toulouse Cedex 4, France Université de Toulouse, UPS, ICT-FR 2599, 31062 Toulouse Cedex 9, France.
Evelyne Chelain EA 4505, LCB (Laboratoire de Chimie Biologique), 5 mail Gay Lussac - Neuville sur Oise, F-95031 Cergy Pontoise Cedex, France
Thierry Brigaud EA 4505, LCB (Laboratoire de Chimie Biologique), 5 mail Gay Lussac - Neuville sur Oise, F-95031 Cergy Pontoise Cedex, France
Remi Chauvin CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, F-31077 Toulouse Cedex 4, France Université de Toulouse, UPS, ICT-FR 2599, 31062 Toulouse Cedex 9, France.

DOI:

https://doi.org/10.17721/fujcV3I1P60-65

Keywords:

butatrienes, carbo-cyclohexadienes, carbo-mers, nucleophilic trifluoromethylation

Abstract

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