Undecenyl resorc[4]arene in the chair conformation as preorganized synthon for olefin metathesis

Francesca Ghirga; Ilaria D'Acquarica; Giuliano Delle Monache; Sara Toscano; Luisa Mannina; Anatoly P. Sobolev; Franco Ugozzoli; Domenico Crocco; Riccarda Antiochia; Bruno Botta

doi:10.1039/C3RA42943A

Undecenyl resorc[4]arene in the chair conformation as preorganized synthon for olefin metathesis†

Francesca Ghirga,^a Ilaria D'Acquarica,*^a Giuliano Delle Monache,^a Sara Toscano,^a Luisa Mannina,^a Anatoly P. Sobolev,^b Franco Ugozzoli,^c Domenico Crocco,^c Riccarda Antiochia^a and Bruno Botta*^a

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^a Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma, P. le Aldo Moro 5, Roma, Italy
E-mail: bruno.botta@uniroma1.it, ilaria.dacquarica@uniroma1.it
Fax: +39 06 49912780
Tel: +39 06 49912781

^b Laboratorio di Risonanza Magnetica “Annalaura Segre”, Istituto di Metodologie Chimiche CNR Area della Ricerca di Roma, Via Salaria km 29.300, Monterotondo, Italy

^c Dipartimento di Chimica Generale, Università di Parma, Parco Area delle Scienze 17/a, Parma, Italy

Abstract

Tetramerization of (E)-2,4-dimethoxycinnamic acid ω-undecenyl ester with ethereal BF₃ gave three stereoisomers 1a, 1b, and 1c, which were assigned as the chair, cone, and 1,2-alternate conformations, respectively. The chair conformation of 1a was confirmed by X-ray diffraction analysis, which also showed a peculiar self-assembly behavior in the crystal lattice, forming intercalated hydrophilic and hydrophobic layers (6–7 Å thickness) as a consequence of strong CH–π interactions. Undecenyl resorc[4]arene 1a, which featured the simplest pattern of substituents, was submitted to olefin metathesis using the second-generation Grubbs complex as the catalyst. Depending on the reaction conditions, different products were isolated: a bicyclic alkene 2a (46%), a linear dimer 3a (5%), and a cross-linked homopolymer P1a (44%).

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Undecenyl resorc[4]arene in the chair conformation as preorganized synthon for olefin metathesis†

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Undecenyl resorc[4]arene in the chair conformation as preorganized synthon for olefin metathesis

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