Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Calixarene Phosphorylation: Cation Control of Reaction Pathways

LT Byrne, JM Harrowfield, DCR Hockless, BJ Peachey, BW Skelton and AH White

Australian Journal of Chemistry 46(11) 1673 - 1683
Published: 1993

Abstract

The hydroxide ion catalysed phosphorylation of p-t- butylcalix [4] arene by diethyl chlorophosphate under heterogeneous conditions shows a marked sensitivity to the nature of the phase transfer catalyst used. Thus, substitution of tetraethylammonium bromide for the tetrabutylammonium bromide prescribed for the synthesis of the calixarene tetraphosphate leads to a major reaction product becoming a bis (phosphate) in which the calixarene binds as a unidentate ligand to one phosphorus and as a bidentate ligand to the other. An X-ray crystal structure analysis on this new compound shows the calixarene to adopt a somewhat distorted 'cone' conformation with an unusual orientation of one of the t-butyl substituents into the cone cavity. It also reveals that a significant diastereoselectivity must operate in the formation reaction. The only other reaction product detected in this system appears to be the calixarene tetraphosphate in a partial cone conformation.

https://doi.org/10.1071/CH9931673

© CSIRO 1993

Committee on Publication Ethics


Export Citation Get Permission

View Dimensions