170167-18-7Relevant academic research and scientific papers
Synthesis and Diels-Alder reactions of 1,2-dimethylene[2.n]metacyclophanes
Yamato, Takehiko,Miyamoto, Shinpei,Hironaka, Tohru,Miura, Yoshinori
, p. 3 - 6 (2005)
(Chemical Equation Presented) The Diels-Alder reaction of 1,2-dimethylene[2.n]MCPs (MCP = metacyclophane) with suitable dienophiles followed by aromatization and photoinduced or FeCl3-induced transannular cyclization afforded phenanthrene-anell
Friedel-Crafts ipso-Acylations of 2-Substituted 4-tert-Butylanisoles and p-tert-Butylmethoxymetacyclophanes
Yamato, Takehiko,Maeda, Kenji,Kamimura, Hideo,Noda, Kozo,Tashiro, Masashi
, p. 1865 - 1889 (2007/10/03)
Acylation of 1,n-bis(5-tert-butyl-2-methoxyphenyl)alkanes 6 with acid chloride or acid anhydride in the presence of Lewis acids afforded only the product arizing from two-fold ipso-acylation at the tert-butyl groups; similar reaction of 1,2-bis(5-tert-butyl-2-methoxy-3-methylphenyl)alkanes 8 led only to the recovery of the starting compounds, thus differing from the nitration of 8 with fuming HNO3 at room temperature which affords in quantitative yield the selective ipso-nitration product at the tert-butyl groups.However, the ipso-acylation reactions of 5,13-di-tert-butyl-8,16-dimethoxymeta-cyclophane 15 led to the first-reported direct introduction of an acyl group due to a through-space electronic interaction with the opposing benzene ring.In contrast the selective ipso-acylation reaction was not observed in the case of the larger ring sized macrocyclic meta-cyclophane, p-tert-butyltetramethoxycalix(4)arene.
