401591-36-4Relevant academic research and scientific papers
Controlled precipitation polymerization of phthalimidomethyloxirane in cationic isomerization ring-opening manner
Kanoh, Shigeyoshi,Nishimura, Tomonari,Mitta, Yasuhiro,Ueyama, Akihiko,Motoi, Masatoshi,Tanaka, Toshiyuki,Kano, Kenji
, p. 651 - 657 (2007/10/03)
The cationic polymerization of phthalimidomethyloxirane (1) with methylaluminum bis-(2,6-di-tert-butyl-4-methylphenoxide) (MAD) afforded polyether (2) or polyacetal (3) depending on temperature. Acetalic linkages in the main chain of 3 were formed via iso
Isomerization of cyclic ethers having a carbonyl functional group: New entries into different heterocyclic compounds
Kanoh, Shigeyoshi,Naka, Masashi,Nishimura, Tomonari,Motoi, Masatoshi
, p. 7049 - 7064 (2007/10/03)
Oxiranes (epoxides) and oxetanes having a carbonyl functional group are chemoselectively isomerized to different heterocyclic compounds via Lewis acid-promoted 1,6- and 1,7-intramolecular nucleophilic attacks of the carbonyl oxygen on the electron-deficient carbon neighboring the oxonium oxygen: for example, cyclic imides to bicyclic acetals, esters to bicyclic orthoesters, sec-amides to 4,5-dihydrooxazole or 5,6-dihydro-4H-1,3-oxazines, and tert-amides to bicyclic acetals or azetidines. The intramolecular attack of a 1,5-positioned carbonyl oxygen predominantly results in a propagating-end isomerization polymerization. On the other hand, cyclic ethers having a 1,8- or farther positioned carbonyl group undergo conventional ring-opening polymerization. A tetrahydrofuran (oxolane) ring does not open, even with a 1,6-positioned carbonyl group.
