Selective Ring-Opening of N-Alkyl Pyrrolidines with Chloroformates to 4-Chlorobutyl Carbamates
- Authors
- Yu, Chunghyeon; Shoaib, Mahbubul Alam; Iqbal, Naeem; Kim, Jun Soo; Ha, Hyun-Joon; Cho, Eun Jin
- Issue Date
- Jul-2017
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.82, no.13, pp 6615 - 6620
- Pages
- 6
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 82
- Number
- 13
- Start Page
- 6615
- End Page
- 6620
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/4223
- DOI
- 10.1021/acs.joc.7b00681
- ISSN
- 0022-3263
1520-6904
- 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.
- Files in This Item
- There are no files associated with this item.
- Appears in
Collections - College of Natural Sciences > Department of Chemistry > 1. Journal Articles
Items in ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.