Tetrahedron letters

A convenient strategy for the synthesis of β, γ-unsaturated aldehydes and acids. A construction of skipped dienes

…, Y Adiyaman, M Adiyaman, WS Powell, GA FitzGerald…

Index: Saha, Goutam; Basu, Manas K.; Kim, Seongjin; Jung, Young-Ju; Adiyaman, Yurdanur; Adiyaman, Mustafa; Powell, William S.; FitzGerald, Garret A.; Rokach, Joshua Tetrahedron Letters, 1999 , vol. 40, # 40 p. 7179 - 7183

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Citation Number: 12

Abstract

In all cases, the double bond migration is easy to recognize as the signal for the two aldehydic protons separate well in the 1 H NMR of the mixtures of isomers. The aldehydic proton of the desired β,γ-unsaturated compounds appears at δ 9.64–9.67 as a broad triplet and the aldehydic proton of the α,β-unsaturated isomers appears as expected upfield at δ 9.52–9.55 as a doublet. The ratio of these two protons gives an accurate indication of the isomerization ...