Tetrahedron

Addition of aminoketene dithioacetals to α, β-unsaturated ketones. Synthesis and reactions of cyclohex-2-en-1, 4-dione monodithioacetals

PCB Page, SA Harkin, AP Marchington, MB van Niel

Index: Page, Philip C. Bulman; Harkin, Shaun A; Marchington, Allan P.; Niel, Monique B. van Tetrahedron, 1989 , vol. 45, # 12 p. 3819 - 3838

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Citation Number: 13

Abstract

Aminoketene dithioacetals add to α, β-unsaturated ketones to give 1, 5-diketones after hydrolytic work-up. Upon treatment with acid or base, these diketones suffer intramolecular aldol reactions yielding cyclohex-2-en-1, 4-dione monodithioacetals, interesting and useful synthetic equivalents of cyclohex-2-en-1, 4-diones which readily undergo conjugate addition and cycloaddition reactions.