Helvetica chimica acta

Ringerweiterung durch Fragmentierung. Synthese von 15??Pentadecanolid (Exaltolid®)

B Milenkov, A Guggisberg, M Hesse

Index: Milenkov, Branimir; Guggisberg, Armin; Hesse, Manfred Helvetica Chimica Acta, 1987 ,  vol. 70, p. 760 - 765

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Citation Number: 20

Abstract

The title compound was synthesized from 1-(3'-hydroxypropyl)-2-oxocyclododecane-1- carbonitrile (3), using two different routes (Scheme). The CN group of 3 was converted to the Me, N+ residue in 5 which underwent, upon NaH treatment, a fragmentation leading to the ring-enlargement product 6. The same product was observed after heating the ring-enlarged dimethylamine oxide 14, prepared from 3 by Bu4NF treatment and conversion of the CN ...