82194-52-3Relevant academic research and scientific papers
Metal cation-exchanged montmorillonite (Mn+-mont)-catalysed aromatic alkylation with aldehydes and ketones
Tateiwa, Jun-Ichi,Hayama, Ei,Nishimura, Takahiro,Uemura, Sakae
, p. 1923 - 1928 (2007/10/03)
The alkylation of aromatic compounds with aldehydes and ketones in the presence of a variety of metal cation-exchanged montmorillonites (Mn+-mont; Mn+ = Zr4+, Al3+, Fe3+, Zn2+, H+, Na+) has been investigated. Al3+- and Zr4+-Monts are revealed to be effective as catalysts, while no reaction takes place with Na+-mont. Al3+-Mont-catalysed alkylation of phenol with several aldehydes produces mainly or almost solely the corresponding gem-bis(hydroxyphenyl)alkanes (bisphenols) in good yields, while that with several ketones affords selectively the corresponding alkylphenols in moderate to good yields. The alkylation always occurs at the carbonyl carbon without any skeletal rearrangement and the kind of products depends much on the steric hindrance of an electrophilic intermediary carbocation. The alkylation of anisole, veratrole and p-cresol proceeds well, while that of toluene, benzene, chlorobenzene and nitrobenzene scarcely occurs.
Regiospecificity in Reactions of Metal Phenoxides. Synthesis of 2,2'-alkylidenebisphenols
Casiraghi, Giovanni,Casnati, Giuseppe,Pochini, Andrea,Ungaro, Rocco
, p. 805 - 808 (2007/10/02)
The reactions between aryloxymagnesium bromides (1) with linear aliphatic aldehydes (2) and their acetals (10) in aprotic solvents of variable donicity have been investigated.In benzene high ortho-regiospecificity is observed in all cases, although with the aldehyde (2) the yield of 2,2'-alkylidenebisphenols (5) is usually low because of the competing aldehyde self-condensation.This process is avoided using diethyl acetals as electrophilic reagents which give the products (5) in good yields.
