85747-57-5Relevant academic research and scientific papers
Concise synthesis of fagaridine and decarine, phenolic benzo[c]phenanthridine alkaloids, using the palladium-assisted biaryl coupling reaction
Harayama, Takashi,Sato, Tomonori,Nakano, Yuichiro,Abe, Hitoshi,Takeuchi, Yasuo
, p. 293 - 301 (2003)
Total synthesis of fagaridine (5) and decarine (6), phenolic benzo[c]phenanthridine alkaloids, was accomplished via the aryl-aryl coupling reaction of bromo amides protected by an isopropyl group with palladium, followed by reduction with LiAlH4/sub
STERIC EFFECTS IN THE METALLATION OF ALKOXY- AND DIALKOXY-BENZENES
Bernard, Angela Maria,Piras, Pier Paolo,Plumitallo, Antonio,Melis, Stefana,Sotgiu, Francesca
, p. 443 - 446 (2007/10/02)
With the aim of examining the role of steric factors in determining the position of metallation, the reaction of n-butyllithium with a series of 1,2-dialkoxy-, 1,2-alkylthio-, 1,4-dialkoxy-, and 2-t-butyl-1-alkoxy-benzenes has been studied in the presence and in the absence of N,N,N',N'-tetramethylethylenediamine (TMEDA).Steric factors are particularly relevant in the case of 2-t-butyl-alkoxybenzenes where the yields of metallation dramatically decrease passing from the methoxy to the isopropoxy derivative, while with the t-butoxy derivative only cleavage of the ether bond occurs.
