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Water‐Soluble Calixarenes as New Inverse Phase‐Transfer Catalysts. Their Scope in Aqueous Biphasic Alkylations and Mechanistic Implications
Author(s) -
Shimizu Shoichi,
Suzuki Takashi,
Shirakawa Seiji,
Sasaki Yasuyuki,
Hirai Choichiro
Publication year - 2002
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200206)344:3/4<370::aid-adsc370>3.0.co;2-3
Subject(s) - chemistry , alkylation , catalysis , aqueous solution , halide , methylene , alkyl , organic chemistry , calixarene , aqueous two phase system , phase (matter) , phase transfer catalyst , combinatorial chemistry , molecule
Alkylation reactions of active methylene compounds, alcohols and phenols with alkyl halides in aqueous NaOH solution can be carried out without the need for any added organic solvents in most cases. The water‐soluble calix[ n ]arenes, which contain trimethylammoniomethyl groups on the upper rim, were used as inverse phase‐transfer catalysts, resulting in the corresponding alkylated products in good to high yields. The scope of this methodology in aqueous biphasic alkylation reactions and the mechanistic implications are discussed.