Canadian journal of chemistry

Preparation and transformations of allenic ketones and 3 (2 H)-furanones

S Wolff, WC Agosta

Index: Wolff, Steven; Agosta, William C. Canadian Journal of Chemistry, 1984 , vol. 62, p. 2429 - 2434

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Citation Number: 14

Abstract

Swern oxidation of allenic alcohols 7 and 10 gives the corresponding ketones 3 and 12. Reaction of 3 with ruthenium tetroxide yields the stable acyl ketene 17 and the acyloxy α- diketone 20 as well as pivalil (4). Formation of 20 by way of the 3 (2 H)-furanone 22 is suggested, since oxidation of 3 and 12 with osmium tetroxide followed by dehydration provides the corresponding furanones 22 and 26 in good yield. Epoxidation of 3 furnishes ...

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