AlCl3 Catalyzed Oxo-Diels-Alder and Wittig-Type Reaction of 2,3-Dimethyl-1,3-Butadiene With Acyl Phosphonates

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Nadeem S., DEMİR A. G.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, vol.189, no.11, pp.1603-1610, 2014 (SCI-Expanded)

• Publication Type: Article / Article
• Volume: 189 Issue: 11
• Publication Date: 2014
• Doi Number: 10.1080/10426507.2014.884089
• Journal Name: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
• Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
• Page Numbers: pp.1603-1610
• Middle East Technical University Affiliated: Yes

Abstract

Different aliphatic and aromatic acyl phosphonates were synthesized using Arbuzov reaction and subjected to Oxo-Diels-Alder (ODA) reaction with 2,3-dimethyl-1,3-butadiene at -78 degrees C. AlCl3 was found the best catalyst to obtain the desired ODA products from acyl phosphonates in only 30min at low temperature, as compared to 100 degrees C-previously reported. The same reaction was repeated at room temperature but, instead of ODA, Wittig-type product was obtained. All the products were characterized by NMR spectroscopy and mass spectrometry. H-1,P-31 and C-13,P-31 couplings were observed in the NMR spectra.