Unsaturated nitriles: precursors for a domino ozonolysis-Aldol synthesis of oxonitriles

FF Fleming, A Huang, VA Sharief…

Index: Fleming, Fraser F.; Huang, Adrian; Sharief, Vaqar A.; Pu, Yifang Journal of Organic Chemistry, 1999 , vol. 64, # 8 p. 2830 - 2834

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Citation Number: 19

Abstract

Cyclic five-, six-, and seven-membered oxonitriles are prepared by a tandem ozonolysis- aldol sequence. Cyclopentenylacetonitrile (4) and cyclohexenylacetonitrile (12) afford the ring-expanded oxonitriles 3 (98%) and 17 (58%), respectively, in highly efficient one-pot syntheses. Homologous five-membered oxonitriles 22a-c are prepared by analogous ozonolysis-aldol cyclizations employing ω-alkenyl β-ketonitriles. The method tolerates ...