Helvetica chimica acta

Acid??Catalysed Rearrangements of α??Vinylcyclobutanones

DA Jackson, M Rey, AS Dreiding

Index: Jackson, David A.; Rey, Max; Dreiding, Andre S. Helvetica Chimica Acta, 1985 , vol. 68, p. 439 - 449

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Citation Number: 16

Abstract

Abstract The BF 3· Et 2 O-and the CH 3 SO 3 H-catalysed rearrangements of 10 α- vinylcyclobutanones have been examined. With little acid, the β, β-dialkyl derivatives 1 were transformed into linear dienones 2 and 3; with more acid, they were converted into cyclopentenones 4 by Nazarov cyclisation of initially formed 2/3. The β-monoalkyl (including the β, γ-dialkyl) derivatives 7 rearranged only with a high acid concentration to afford the ...