Tetrahedron

Generation of dienone and trienone dianion derivatives: Double deprotonation as a route to lumo-filled π-systems

D Seebach, M Pohmakotr

Index: Seebach, Dieter; Pohmakotr, Manat Tetrahedron, 1981 , vol. 37, # 23 p. 4047 - 4058

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Citation Number: 26

Abstract

Conjugated unsaturated carbonyl compounds and their analogues 1 are a1, 3, 5...-reagents. An umpolung of this intrinsic reactivity can be achieved by generation of the dianions 2, LUMO filled π-systems, from hydrogenated precursors, see schemes 1 and 2. The preparation of the allylated ketones 3a–d, of the acid derivatives 3e–h, 9, 10, 12 as well as of the dienones 11 is described. Their double deprotonation (→ 14, 18, 26, 30, 33, 36, and ...