Unusual Reactivity of Aryl Aldehydes with Triethyl Phosphite and Zinc Bromide: A Facile Preparation of Epoxides, Benzisoxazoles, and α-Hydroxy Phosphonate Esters

Author： Raju Potharaju   Gobi Rajeshwaran Ganesan   Nandakumar Meganathan   Mohanakrishnan Arasambattu K.  

Publisher： Blackwell Publishing

E-ISSN： 1099-0690|2015|16|3513-3523

ISSN： 1434-193X

Source： European Journal of Organic Chemistry, Vol.2015, Iss.16, 2015-06, pp. : 3513-3523

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Abstract

A facile preparation of trans-epoxides was achieved by a (EtO)3P–ZnBr2-mediated deoxygenation reaction of the corresponding 2-nitrobenzaldehydes. The sterically hindered analogues of 2-nitrobenzaldehyde underwent a reaction with triethyl phosphite in the presence of ZnBr2 as the catalyst to form benzisoxazoles as the sole product. Under identical conditions, the reactions of electron-rich as well as moderately electron-deficient aryl aldehydes furnished the corresponding α-hydroxy phosphonate esters. A (EtO)3P–ZnBr2-mediated deoxygenation reaction of 2-nitrobenzaldehydes was developed for the facile preparation of trans-epoxides. When sterically hindered 2-nitrobenzaldehydes were treated with triethyl phosphite and ZnBr2, benzisoxazoles were formed as the sole product. Electron-rich and moderately electron-deficient aryl aldehydes gave α-hydroxy phosphonate esters under identical conditions.

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