Identification of Reactive Intermediates for the Decarbonylative Reaction of 1-Alkylprolines

Yu Chiao Shih, Jing Shiuan Wang, Chia Chun Hsu, Pei Hua Tsai, Tun Cheng Chien*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)


1-Alkylprolines undergo decarbonylative reactions with oxalyl chloride and subsequent Mannich reactions with nonactivated C-H nucleophiles to give 2-substituted pyrrolidines as Mannich adducts. We showed that 1-alkyl-1-pyrrolinium compounds are the reactive intermediates formed by the decarbonylative reactions of 1-alkylprolines. Our results also confirmed that an azomethine ylide, although unreactive toward the Mannich reaction and not involved in the decarbonylative Mannich reaction, can be generated by deprotonation of the corresponding 1-alkyl-1-pyrrolinium compound under mild conditions.

Original languageEnglish
Article numberst-2016-u0387-l
Pages (from-to)2841-2845
Number of pages5
Issue number20
Publication statusPublished - 2016 Dec 15


  • azomethine ylides
  • electrophilic aromatic substitution
  • Mannich reaction
  • pyrrolidines
  • pyrrolinium compounds

ASJC Scopus subject areas

  • Organic Chemistry


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