1,7-Dioxaspiro[5.5]undecanes. An excellent system for the study of stereoelectronic effects (anomeric and exo -anomeric effects) in acetals

Abstract

Several isomeric compounds derived from the spiro systems 5 to 9 (Scheme 4) were obtained from the acid cyclization of the appropriate dihydroxy ketone precursor.The configuration and the conformation of the products obtained was determined by 13 C nmr analysis and equilibration studies. The experimental results can be rationalized by taking into account the anomeric and the exo-anomeric effects and the usual steric interactions.