25387-01-3Relevant academic research and scientific papers
Water-Soluble Calixarenes as New Inverse Phase-Transfer Catalysts. Their Scope in Aqueous Biphasic Alkylations and Mechanistic Implications
Shoichi, Shimizu,Suzuki, Takashi,Shirakawa, Seiji,Sasaki, Yasuyuki,Hirai, Choichiro
, p. 370 - 378 (2007/10/03)
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.
Formation and Reactions of 1-Phenyl-2-propanone Dianion and Related Systems with Electrophilic Reagents
Trimitsis, G. B.,Hinkley, J. M.,TenBrink, R.,Faburada, A. L.,Anderson, R.,et al.
, p. 2957 - 2962 (2007/10/02)
1-Phenyl-2-propanone, 1,1-diphenyl-2-propanone, and 1-(4-methoxyphenyl)-2-propanone were converted to their dicarbanions 3, 4, and 31, respectively, and their reactions with a number of electrophilic reagents were examined.All three dianions gave a mixture of C-1 and C-3 alkylation products when treated with alkyl halides of higher reactivity, while only C-1 alkylations occurred when alkyl halides of lower reactivity were used.It was also found that the 1,1-diphenyl-2-propanone and the 1-(4-methoxyphenyl)-2-propanone dianions 4 and 31 gave a higher ratio of C-1/C-3 alkylation products than the 1-phenyl-2-propanone dianion 3.When dianion 3 was reacted with p-anisaldehyde and a number of protonating agents, electrophilic attack occurred exclusively at the C-3 position.The trends observed are analyzed, and mechanisms are proposed to account for the results obtained.
