Synthesis, characterization and X-ray crystallography study of stable ylide of di-tert-butyl-2-(2-indolinon-1-yl)-3-(trimethoxyphosphorane ylidene) butanedioate

Autor: Seyed Sajad Sajadikhah, Ghobad Mansouri, Faramarz Rostami-Charati, Mohamed Makha, Massoud Ghobadi
Jazyk: English<br />Persian
Rok vydání: 2023
Předmět:
Zdroj: شیمی کاربردی روز, Vol 18, Iss 66, Pp 147-158 (2023)
Druh dokumentu: article
ISSN: 2981-2437
DOI: 10.22075/chem.2022.24342.2008
Popis: Stable ylide of di-tert-butyl-2-(2-indolinon-1-yl)-3-(trimethoxyphosphorane ylidene) butanedioate was synthesized by means of catalyst-free reaction of trimethyl phosphite, di-tert-butylacetylene dicarboxylate and 2-indolinone in n-hexane/diethyl ether at ambient temperature. Obtained product was characterized by 1H, 13C, 31P NMR, FT-IR and mass spectroscopy. The crystal structure of the stable ylide was determined by X-ray crystallography. The title compound crystallized in monoclinic, space group P21/c and cell parameters a=15.8079(7) Å, b= 18.7521(13) Å, c =17.4987(10) Å, β= 95.504(6)° and Z=8. The X-ray study showed that adjacent carbonyl group (C291=O291, C191=O191) in the ylide moiety of compound had a resonance with bond of C=P. These results show clearly that environment of C(19, 29) is planar.
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