A new 2-azatricyclo [4.4. 0.02, 8] decenone synthesis and ketene formation by retro-Diels-Alder reaction

AG Schultz, JP Dittami, SO Myong…

Index: Schultz,A.G.; Dittami,J.P.; Myong,S.U. Journal of the American Chemical Society, 1983 , vol. 105, p. 3273

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Citation Number: 40

Abstract

Abstract: 6-(3-Azidopropyl)-2, 4-cyclohexadien-1-ones 2c and Zd and 6-(o-azidobenzyl)-2, 4- cyclohexadien-1-ones 7a and 7b are prepared by C-alkylation of 2, 4, 6-trialkyl-substituted phenols. These azides provide triazolines 3a, 3b, Sa, and 8b by thermal intramolecular azide-olefin cycloaddition. Photochemical conversion of triazolines to 2-azatricyclo [4.4. O. O2~*] dec-9-en-7-ones 4a, 4b, and 10a with 366-nm light accomplished the synthetic ...