J. Tateiwa et al., CATION-EXCHANGED MONTMORILLONITE (M(N-MONT)-CATALYZED PRINS REACTION()), Bulletin of the Chemical Society of Japan, 69(8), 1996, pp. 2361-2368
The Prins reaction of styrenes with paraformaldehyde or 1,3,5-trioxane
in toluene in the presence of cation-exchanged montmorillonite (M(n+)
-mont), which worked as a Bronsted acid catalyst, at 80 degrees C prod
uced 4-aryl-1,3-dioxanes selectively in up to 99% isolated yield with
a turnover number of up to 5.9 x 10(2). Among the examined 21 M(n+)-mo
nts, Ce3+- and Fe3+-monts were revealed to be quite effective. Regener
ation of the catalyst was confirmed with the Ce3+-mont, which could be
effectively recycled at least three times. Many lanthanide metal ion-
exchanged montmorillonites (Ln(3+)-monts) were prepared and characteri
zed by X-ray powder diffraction (XRD) and temperature-programmed desor
ption of ammonia gas (NH3-TPD) methods.