J. A. Rompes, S. Hoff, P. P. Montijn
Sep 2, 2010
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Recueil des Travaux Chimiques des Pays-Bas
Abstract
Treatment of the carbinols (CH3)2C=C=C=C(OCH3)CR1R2(OH) (I) with potassium tert-butoxide in dimethyl sulfoxide gives derivatives of furan (III) if R2 = H and derivatives of 2,5-dihydrofuran (II) if R1 and R2 are both alkyl or if R1R2C = cyclohexyl. Acid-catalysed hydrolysis of II and III affords derivatives of 3-oxo-2,3-dihydrofuran (IV). Potassium amide in liquid ammonia, when used in excess, causes isomerisation of I into CH2=C(CH3)CH=C=C(OCH3)CR1R2(OH) (Ia).