TITLE

Selective chemistry of tripentaerythritol — Synthesis of acetals and their derivatives

AUTHOR(S)
Al-Mughaid, Hussein; Grindley, T. Bruce
PUB. DATE
April 2006
SOURCE
Canadian Journal of Chemistry;Apr2006, Vol. 84 Issue 4, p516
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
Tripentaerythritol was converted efficiently into 2′,2′′:6′,6′′:10′,10′′-tri-O-cyclohexylidene-2,2,6,6,10,10-hexakis(hydroxymethyl)-4,8-dioxa-1,11-undecandiol (4) by the toluenesulfonic acid catalysed reaction with cyclohexanone in a mixture of N,N-dimethylformamide and benzene. Reaction of tripentaerythritol with benzaldehyde under similar conditions gave an easily separated mixture of the four possible stereoisomers. Structures of these stereoisomers were assigned based on 1H and 13C NMR chemical shifts using trends previously observed for the dibenzylidene acetals of dipentaerythritol, whose structures had been established unambiguously by X-ray crystallography. It was found that reduction of the mixture of benzylidene acetals to 2,6,10-tris(benzyloxymethyl)-4,8-dioxa-1,11-undecanediol could be accomplished using triethylsilane with ethylaluminium dichloride as the Lewis acid after a number of commonly used conditions for this transformation failed.
ACCESSION #
21197108

 

Share

Read the Article

Courtesy of VIRGINIA BEACH PUBLIC LIBRARY AND SYSTEM

Sorry, but this item is not currently available from your library.

Try another library?
Sign out of this library

Other Topics