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

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

来源：RSC Advances, 2013, 3(38): 17567-17576.

DOI：10.1039/c3ra42943a

Tetramerization of (E)-2,4-dimethoxycinnamic acid v-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 angstrom thickness) as a consequence of strong CH-pi 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%).

• 出版日期2013