222192-40-7Relevant academic research and scientific papers
Medium-sized cyclophanes - Part 85: Benzylation by 8-(bromomethyl)[2.2] metacyclophanes. Through-space electronic interactions of [2.2]metacyclophane benzyl cations
Shimizu, Tomoe,Tanaka, Kan,Paudel, Arjun,Yamato, Takehiko
, p. 458 - 462 (2010)
TiCl4-mediated Friedel-Crafts benzylation of benzene with 8-(bromomethyl)[2.2]metacyclophanes to afford 8-benzyl[2.2]metacyclophanes is described. Substituent effect through space on the rate of the benzylation of benzene with a bromomethyl group attached on the opposite aromatic ring was first found in this investigation. Interestingly, the introduction of the substituents at the internal position 16 tends to promote the present benzylation reaction rate 1.8-3.8 times. It was found that the benzyl cation intermediate was stabilized by the the direct through-space cation-π interaction among the opposite benzene ring in the benzylation of [2.2] metacyclophane systems.
