β??Cleavage of Bis (homoallylic) Potassium Alkoxides. Two??Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar??Turmerone, α??Damascone, …

RL Snowden, SM Linder, BL Muller…

Index: Snowden, Roger L.; Linder, Simon M.; Muller, Bernard L.; Schulte, Karl H. Helvetica Chimica Acta, 1987 , vol. 70, p. 1858 - 1878

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Citation Number: 34

Abstract

Abstract The transformation of 36 bis (homoallylic) alcohols VII to alkenones IX and Xvia β- cleavage of their potassium alkoxides VIIa in HMPA has been investigated (cf. Scheme 2). These studies have established an order of β-cleavage for 2-propenyl, 1-methyl-2propenyl, 2-methyl-2-propenyl, 1, 1-dimethyl-2propenyl, and benzyl groups in alkoxides 49a–56a and have allowed a comparison between the β-cleavege reaction and the oxy-Cope ...

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