107485-06-3Relevant academic research and scientific papers
Cationic Cyclocodimerization. 4. Syntheses and Structures of Metacyclophane Derivatives. Cyclization Controlled by an Orbital Interaction and a Steric Constraint
Nishimura, Jun,Ohbayashi, Akihiro,Horiuchi, Yuzuru,Okada, Yuhikiro,Yamanaka, Shun-ichi,Oku, Akira
, p. 1409 - 1413 (2007/10/02)
Cationic cyclocodimerization of α,ω-bis(m-vinylphenyl)alkanes and 1-(m-vinylphenyl)-3-(p-vinylphenyl)propane with some comonomers were carried out.The reactions of α,ω-bis(m-vinylphenyl)alkanes gave metacyclophanes in 30-59percent yields.The structures of the metacyclophanes were determined by chemical shift differences between intraannular and extraannular protons, VT NMR spectroscopic measurements, and NOE experiments.Cyclocodimerizations of 1,3-bis(m-vinylphenyl)propane with several comonomers gave primarily two cyclophanes, although eight isomers are possible.Both 1,4-bis(m-vinylphenyl)butane and 1,5-bis(m-vinylphenyl)pentane cyclocodimerized with styrene to form exo,cis-1-methyl-3-styryl-anti-metacyclophane as the major product.This selectivity is explained by molecular orbital calculation and examination of molecular models.The stabilities of intramolecularly face-to-face associated cations are discussed in relation to the reaction mechanism.
Coupling Reaction of Grignard Reagents with α,ω-Dibromoalkanes in the Presence of Copper(I) Bromide-HMPA: Preparation of α,ω-Bis(vinylaryl)alkanes
Nishimura, Jun,Yamada, Noriyuki,Horiuchi, Yuzuru,Ueda, Eiji,Ohbayashi, Akihiro,Oku, Akira
, p. 2035 - 2037 (2007/10/02)
The coupling reaction of Grignard reagents with α,ω-dibromoalkanes took place smoothly in THF/HMPA (12:1) in the presence of a catalytic amount of copper(I) bromide and gave the products in 60-100 percent yields.Several α,ω-bis(vinylaryl)alkanes were prepared in reasonable yields by the application of this reaction.
