ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis of new trisubstituted hexahydro-isoindole-1,3-dione derivatives regio- and stereoselectivity: spectroscopic and theoretical studies

Özlem Gündoğdu

Vocational School of Kaman, Kırşehir Ahi Evran University, Kırşehir, Turkey

E-mail: ogundogdu@ahievran.edu.tr

Received: 24 October 2022  Accepted: 28 December 2022

Abstract:

Abstract

2-Hydroxy-5-alkylhexahydro-4H-oxireno[2,3-e]isoindole-4,6(5H)-diones were synthesized, and their C-2 selective ring-opening products were obtained through nucleophilic additions such as with MeOH. The methoxydiols obtained from the ring-opening reactions were converted to corresponding acetate derivatives. The structures of the methoxydiacetates were determined by ¹H and ¹³C NMR and X-ray analyses. Furthermore, theoretical computations were carried out to explain the regioselectivity in the ring-opening reaction of epoxy alcohols. The theoretical calculations showed that the ring-opening reaction of epoxy alcohols proceeds in a thermodynamically controlled manner and regioselectivity occurs depending on the stability of the intermediate.

Graphical Abstract

Keywords: Isoindole-1,3-diones; Ring-opening reaction; Thermodynamically controlled; Regioselectivity; Epoxy alcohol

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02657-4

Chemical Papers 77 (5) 2679–2687 (2023)