Tri-w-propylamine

PA = 226 kcal mol-1), the predominant formation (6.4 to 1) of the (/ ,.S )-di-2-hutyl ether over the (R,R)- and (S,S)-forms is attributed to a simple backside displacement in the proton-bound adduct of the starting 2-butanol enantiomer with inversion of configuration of the reaction site and loss of a molecule of water. When tri-w-propylamine is replaced by the less basic NH3 (PA = 196 kcal mol-1), fast neutralization of the proton-bound dimers of the starting 2-butanol is prevented and, therefore, they can grow, producing aggregates that resemble solution microenvironments in which S l pathways may be accessible as well. In them or in their primary substituted derivatives, consecutive nucleophilic displacements may take place. As a consequence, the stereospecificity of the process is lost and the [(/ ,5)-di-2-butyl ether]/[(/ ,/ )- and (S,S)-di-2-butyl ethers] ratio falls down to 1.2. In this case,... 

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