Journal of Organic Chemistry 2003-10-17

2-azabicyclo[2.2.2]octa-3,5-dione via a nitrile Diels-Alder reaction.

Cynthia K McClure, Jeffrey S Link

Index: J. Org. Chem. 68(21) , 8256-7, (2003)

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Abstract

The hetero-Diels-Alder reaction of an electron-deficient nitrile, p-toluenesulfonyl cyanide, with the silyl enol ether of cyclohexenone produced a hydrolytically sensitive [4 + 2] adduct in good yield. Use of Mander's reagent, ethyl cyanoformate, with the same diene, produced an unstable adduct. Hydrolysis of the tosyl cyanide adduct resulted in the isoquinuclidinone 2-aza[2.2.2]octa-3,5-dione as a crystalline compound in excellent yield from the nitrile.