On Rh-2(OAc)(4)-catalysed decomposition of 1-diazo-4-(2-methoxyphenyl)butan-2-one (9) and its methyl-substituted analogue (18), norcaradienones 10 and 19, respectively, were observed as the only regioisomers resulting from intramolecular cyclopropanation, indicative of attack by the metal carbene away from the methoxy group; to explain the transformation of 10 and 19 into dihydroazulenones 15 and 23, interconversion of 10 and 19 into their isomers 14 and 22 must be invoked, and an ionic 'ring-walk' rearrangement is suggested for such an isomerization.
A reinvestigation of the Rh-2(OAc)(4)-catalysed decomposition of 1-diazo-4-(2-methoxyphenyl)alkan-2-ones: evidence for ionic 'ring-walk' rearrangement in norcaradiene derivatives / P. Manitto, D. Monti, S. Zanzola, G. Speranza. - In: CHEMICAL COMMUNICATIONS. - ISSN 1359-7345. - 1999:6(1999 Mar), pp. 543-544. [10.1039/a809991j]
A reinvestigation of the Rh-2(OAc)(4)-catalysed decomposition of 1-diazo-4-(2-methoxyphenyl)alkan-2-ones: evidence for ionic 'ring-walk' rearrangement in norcaradiene derivatives
P. Manitto
Primo
;G. SperanzaUltimo
1999
Abstract
On Rh-2(OAc)(4)-catalysed decomposition of 1-diazo-4-(2-methoxyphenyl)butan-2-one (9) and its methyl-substituted analogue (18), norcaradienones 10 and 19, respectively, were observed as the only regioisomers resulting from intramolecular cyclopropanation, indicative of attack by the metal carbene away from the methoxy group; to explain the transformation of 10 and 19 into dihydroazulenones 15 and 23, interconversion of 10 and 19 into their isomers 14 and 22 must be invoked, and an ionic 'ring-walk' rearrangement is suggested for such an isomerization.File | Dimensione | Formato | |
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