Selective Ring-Opening of N-Alkyl Pyrrolidines with Chloroformates to 4-Chlorobutyl Carbamates
DC Field | Value | Language |
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dc.contributor.author | Yu, Chunghyeon | - |
dc.contributor.author | Shoaib, Mahbubul Alam | - |
dc.contributor.author | Iqbal, Naeem | - |
dc.contributor.author | Kim, Jun Soo | - |
dc.contributor.author | Ha, Hyun-Joon | - |
dc.contributor.author | Cho, Eun Jin | - |
dc.date.available | 2019-03-08T08:37:00Z | - |
dc.date.issued | 2017-07 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.issn | 1520-6904 | - |
dc.identifier.uri | https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/4223 | - |
dc.description.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. | - |
dc.format.extent | 6 | - |
dc.language | 영어 | - |
dc.language.iso | ENG | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | Selective Ring-Opening of N-Alkyl Pyrrolidines with Chloroformates to 4-Chlorobutyl Carbamates | - |
dc.type | Article | - |
dc.identifier.doi | 10.1021/acs.joc.7b00681 | - |
dc.identifier.bibliographicCitation | JOURNAL OF ORGANIC CHEMISTRY, v.82, no.13, pp 6615 - 6620 | - |
dc.description.isOpenAccess | N | - |
dc.identifier.wosid | 000405358000011 | - |
dc.identifier.scopusid | 2-s2.0-85022185157 | - |
dc.citation.endPage | 6620 | - |
dc.citation.number | 13 | - |
dc.citation.startPage | 6615 | - |
dc.citation.title | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.citation.volume | 82 | - |
dc.type.docType | Article | - |
dc.publisher.location | 미국 | - |
dc.subject.keywordPlus | TERTIARY-AMINES | - |
dc.subject.keywordPlus | ACID-CHLORIDES | - |
dc.subject.keywordPlus | DEALKYLATION | - |
dc.subject.keywordPlus | DENSITY | - |
dc.subject.keywordPlus | MILD | - |
dc.subject.keywordPlus | DERIVATIVES | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Organic | - |
dc.description.journalRegisteredClass | sci | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
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