Article 2022 · 7 atıf

Regio- and stereo-chemical ring-opening reactions of the 2,3-epoxy alcohol derivative with nucleophiles: Explanation of the structures and C-2 selectivity supported by theoretical computations

Gundogdu, Ozlem, Atalay, Abdurrahman, Celebioglu, Neslihan, Anil, Baris, Sahin, Ertan, Sanli-Mohamed, Gulsah, Bozkaya, Ugur, Kara, Yunus

Özet

The ring-opening reactions of (1aS,2S,6bR)-5-ethyl-2-hydroxyhexahydro-4H-oxireno[2,3-e]isoindole-4,6(5H)-dione were investigated under very mild and nonchelated conditions. C-2 selective ring-opening products were obtained with nucleophilic additions such as Cl-, Br- and N-3(-). The exact configuration of (3aS,4R,5R,6S,7aS)-5-chloro-2-ethyl-4,6-dihydroxyhexahydro-1H-isoindole-1,3(2H)-dione was determined by X-Ray diffraction analysis which was obtained from the reaction of epoxy alcohol with HCl . On the other hand, theoretical computations were carried out to explain the regioselectivity in the ring opening reaction of epoxy alcohols. The results showed that the ring-opening reaction of both epoxy alcohols proceeds in a kinetically controlled manner and regioselectivity occurs depending on the transition state. (c) 2022 Published by Elsevier B.V.

Anahtar Kelimeler

Epoxy alcohol Ring opening Regioselectivity Theorical computations Isoindole-1,3-dione SUBSTITUTION-REACTIONS REARRANGEMENT 1,2-EPOXIDES MECHANISMS ACIDS

WoS Kategorileri

Chemistry, Physical

Sürdürülebilir Kalkınma Amaçları

Sağlık ve Kaliteli Yaşam

Künye

Dergi: JOURNAL OF MOLECULAR STRUCTURE
Yıl: 2022
Cilt: 1264
ISSN: 0022-2860
eISSN: 1872-8014
DOI: 10.1016/j.molstruc.2022.133163
WoS UID: WOS:000805644900007

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