
%0 Journal Article
%A Dainis, I 
%T Indolizines. IV. Reductive cleavage of acyl groups from acetylindolizines. C-Protonation and fragmentation of Indolizine-3-carbinols
%J Australian Journal of Chemistry
%D 1972/09/01
%V 25
%N 9
%P 2013-2020
%K 
%R https://doi.org/10.1071/CH9722013
%U https://www.publish.csiro.au/paper/CH9722013 
%X Sodium borohydride in ethanol has effected cleavage of 3-acetylindolizines to indolizines in those cases where the intermediate 3-carbinols are readily protonated at C3. Reduction of 3-acetyl-2-methylindolizine in EtOD has demonstrated that fragmentation proceeds via C-protonation, and has also provided a selective method for the 3-deuteration of reactive indolizines. 1-Acetyl- and 1,3-diacetyl-indolizines gave unstable product mixtures on reduction excepting the one case where the product carbinol was stabilized by a resistant, electron-withdrawing 3-substituent. 3-Ethoxyoarbonyl groups were not affected. 
