85686-10-8Relevant articles and documents
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.