AcCl veya Ac2O Kullanılarak Bazı Norkantarimid Türevlerinin Moleküler Kararlılık, Sentez Mekanizması ve Oluşumunlarının İncelenmesi: Mekanizma Tabanlı Bir Çalışma

Year 2023, Volume: 23 Issue: 3, 618 - 627, 28.06.2023

Aytekin Köse

https://doi.org/10.35414/akufemubid.1207578

Abstract

Bu çalışmadaki amaç, ilk olarak norkantarimid türevlerinin AcCl ile eter parçalanmasından sonra oluşan diasetatların zamanla klorlu monoasetatlara dönüşümünü NMR tekniği yardımıyla detaylı olarak açıklamak ve ikinci olarak bu dönüşümü teorik ve hesaplamalı olarak doğrulamaktır. N-metil, N-benzil ve N-asetoksietil sübstitüe norkantarimid türevlerinin eter parçalanma reaksiyonları Ac2O veya AcCl ile H2SO4 varlığında gerçekleştirildi ve bu reaksiyonların mekanizmaları detaylı olarak açıklandı. AcCl ile yapılan reaksiyonlardan alınan örneklerin 1H NMR analizlerine göre, önce trans-1,4-diasetatlar oluştu. Reaksiyonun devam etmesi ile trans-1,4-diasetatlar, SN2' mekanizması yoluyla trans-1,2-kloroasetatlara dönüştü. İlave olarak, bu açıklama teorik ve fiziksel hesaplamalarla daha da desteklendi.

Keywords

Klorlanmış ürünler;, Norkantarimid, Aminler, SN2' mekanizması

Investigation Into The Molecular Stability, Synthesis Mechanism, and Formation of Some Norcantharimide Derivatives Using AcCl or Ac2O: A Mechanism-Based Study

Abstract

The aim in this study was first to explain, in detail the conversion of diacetates over time into chlorinated monoacetates following ether cleavage with AcCl of norcantharimide derivatives with the help of the NMR technique and second, to verify this conversion theoretically and computationally. Ether cleavage reactions of N-methyl, N-benzyl, and N-acetoxyethyl-substituted norcantharimide derivatives were performed with Ac2O or AcCl in the presence of H2SO4, and the mechanisms of these reactions were elucidated in detail. According to the 1H NMR analyses of aliquots from the reactions with AcCl, trans-1,4-diacetates formed firstly. Upon the continuation of the reaction, trans-1,4-diacetates transformed into trans-1,2-chloroacetates via an SN2' mechanism. Additionally, this explanation was further supported by the soft theoretical and physical calculations.

Keywords

Chlorinated products, Norcantharimide, Amines, SN2' mechanism

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