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Short Communication

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

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Pages 1603-1610 | Received 09 Apr 2013, Accepted 09 Nov 2013, Published online: 21 Oct 2014
 

GRAPHICAL ABSTRACT

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°C. AlCl3 was found the best catalyst to obtain the desired ODA products from acyl phosphonates in only 30 min at low temperature, as compared to 100°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. 1H,31P and 13C,31P couplings were observed in the NMR spectra.

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