|
Type |
Poster Presentation |
Area |
Organic Chemistry |
Room No. |
Event Hall |
Time |
4월 19일 (목요일) 11:00~12:30 |
Code |
ORGN.P-386 |
Subject |
Selective Ring-Opening of N‑Alkyl Pyrrolidines with Chloroformates to 4‑Chlorobutyl Carbamates |
Authors |
ChungHyeon Yu, Hyun-Joon Ha1, Eun Jin Cho2,* Department of Bionanotechnology, Hanyang University, Korea 1Department of Chemistry, Hankuk University of Foreign Studies, Korea 2Department of Chemistry, Chung-Ang University, Korea |
Abstract |
Our study shows that among aza-heterocycles of various ring sizes, including aziridines, azetidines, pyrrolidines, and piperidines, only N-alkyl pyrrolidines undergo competitive reaction pathways with chloroformates to yield N-dealkylated pyrrolidines and 4-chlorobutyl carbamates. The pathway taken depends on the substituent on the nitrogen, i.e., ring-opening with methyl and ethyl substituents and dealkylation with a benzyl substituent. Computational calculations support the substituent-dependent product formation by showing the energy difference between the transition states of both reaction pathways. Selective ring-opening reactions of N-methyl and N-ethyl pyrrolidine derivatives with chloroformates were utilized to prepare various 4-chlorobutyl carbamate derivatives as valuable 1,4-bifunctional compounds. |
|
|
E-mail |
cndvkdi@naver.com |
|