
TY  - JOUR
A1  - Dainis, I 
T1  - Indolizines. IV. Reductive cleavage of acyl groups from acetylindolizines. C-Protonation and fragmentation of Indolizine-3-carbinols
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1972
VL  - 25
IS  - 9
SP  - 2013
EP  - 2020
KW  - 
UR  - https://doi.org/10.1071/CH9722013 
N2  - 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. 
ER  -

