114012-43-0Relevant articles and documents
A new and versatile synthesis of 3-substituted oxetan-3-yl methyl alcohols
Boyd, Scott,Davies, Christopher D.
, p. 4117 - 4119 (2014/07/22)
We have developed a novel route for the efficient synthesis of pharmaceutically significant 3-substituted oxetan-3-yl methyl alcohols starting from readily available malonates. The synthesis harnesses the diversity of malonate chemistry and allows access to a range of oxetanes, which exemplifies the versatility of this procedure.
Unusual cyclodimerization of small cyclic ethers via neighboring carbonyl-group participation and cation transfer
Kanoh, Shigeyoshi,Nishimura, Tomonari,Naka, Masashi,Motoi, Masatoshi
, p. 7065 - 7074 (2007/10/03)
Oxetanes having both a carbonyl functional group and a phenyl group at the 3-position bring about unusual cyclodimerization under the influence of trifluoromethanesulfonic acid, to give a cis/trans-isomer mixture of substituted 1,3-dioxanes via neighboring carbonyl-group participation, cation transfer including phenonium rearrangement, and cyclodimerization. Oxiranes having a carbonyl functional group also undergo a similar cyclodimerization to form a 1,3-dioxolane ring. No phenyl substituent is required in the cases of the oxiranes, because the cation transfer process involves a 1,2-hydride shift alone. These five- and six-membered cyclic acetals are quite different from ring-expanded cyclic ether dimers expected simply from the back-biting reaction known in the cationic ring-opening polymerization of oxiranes and oxetanes.
