135288-40-3Relevant academic research and scientific papers
On the Origin of the Distal vs. Proximal Regioselectivity in Di-O-alkylation of Calixarenes
Araki, Koji,Iwamoto, Koji,Shigematsu, Satoshi,Shinkai, Seiji
, p. 1095 - 1098 (1992)
The mechanistic basis of the distal vs. proximal regioselectivity in di-O-alkylation of calixarene was investigated through the detailed product analyses.It was found that (i) the regioselectivity is profoundly affected by the residual intramolecular h
Stereoselective dialkylation of the proximal hydroxy groups of calix- And thiacalix[4]arenes
Narumi, Fumitaka,Hattori, Tetsutaro,Morohashi, Naoya,Matsumura, Nobuji,Yamabuki, Waka,Kameyama, Hiroshi,Miyano, Sotaro
, p. 890 - 898 (2007/10/03)
Treatment of p-tert-butylcalix[4]arene (C1) and its sulfur-bridged analog T1 with 1,3-dichloro-1,1,3,3-tetraiso-propyldisiloxane in the presence of imidazole gives proximally O,O′-disiloxane-1,3-diyl-bridged calixarenes C2 and T2 in excellent yields, resp
syn-1,2-dialkylated calix[4]arenes: General intermediates in the NaH/DMF tetraalkylation of calix[4]arenes
Groenen,Ruel,Casnati,Timmerman,Verboom,Harkema,Pochini,Ungaro,Reinhoudt
, p. 2675 - 2678 (2007/10/02)
In DMF or acetonitrile with NaH as a base at room temperature the tetraalkylation of calix[4]arenes 1a and 1b proceeds via the syn-1,2-disubstituted products to the tetraalkylated calix[4]arenes in the cone conformation. With KH as a base the tetraalkylated calix[4]arenes are predominantly formed in the partial cone conformation, and the reaction proceeds via both the syn-1,3-di and the syn-1,2-disubstituted products. Also the solvent influences the pathway via which tetraalkylation takes place. The syn-1,2-disubstituted calix[4]arenes 2-6 can be isolated in 15-55% from the NaH/DMF or MeCN reactions when only 2.2 equiv of the electrophile are used.
