
%0 Journal Article
%A Crank, G 
%A Eastwod, FW 
%T Derivatives of orthoacids. I. Bicyclic orthoesters
%J Australian Journal of Chemistry
%D 1964/12/01
%V 17
%N 12
%P 1385-1391
%K 
%R https://doi.org/10.1071/CH9641385
%U https://www.publish.csiro.au/paper/CH9641385 
%X Ethyl orthoformate reacts with butane-1,2,4-triol, pentane-1,2,5-triol, and pentane-1,3,5-triol to form 2,7,8-trioxabicyclo[3,2,1]octane, 2,8,9-trioxabicyclo[4,2,1]nonane, and 2,8,9-trioxabicyclo[3,3,1]nonane respectively. Attempts to prepare the analogous bicyclic orthoesters from glycerol and 2-hydroxymethyl-butane-1,4-diol led to monocyclic derivatives and to polymers. The ease of formation and stability of these bicyclic compounds are contrasted with those of 4-methyl-2,6,7-trioxabicyclo[2,2,2]octane and the results are discussed in relation to the stereochemistry of the transition state in ester and amide hydrolysis. 
