- A simple synthesis of acetyl and propionyl cyclododecanes
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1-Formyl-4,8-cyclododecadiene, obtained by hydroformylation of 1,5,9-cyclodecatriene, reacts with MeMgHal or EtMgHal to give 1-(1'-hydroxyethyl)- or 1-(1'-hydroxypropyl)-4,8-cyclodecadiene, respectively.The hydrogenation of their double bonds and subsequent oxidation of the resulting alcohols afford, in high yields, acetyl- or propionylcyclododecane, respectively.
- Zakharkin, L. I.,Guseva, V. V.,Antonova, G. N.
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- Musk-like scents and their manufacture
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New 1-acyl- and 1-hydroxymethyl-cyclododecanes and -cyclododecenes. The new 1-acyl-cyclododecenes and -cyclododecanes are obtained by a Rupe or Meyer-Schuster rearrangement, with or without subsequent hydrogenation in the presence of Ni, Pd and Pt catalysts. The 1-acyl-cyclododecenes and -cyclododecanes are valuable scents of the basic type of the sought-after macrocyclic musk scents. Furthermore, they are used for the manufacture of numerous other new 1-substituted or 1-and 2-substituted cyclododecenes and cyclododecanes having good scent characteristics.
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- Wanderungstendenzen cyclischer, polycyclischer und methylverzweigter Alkylreste bei der Beckmann-Umlagerung
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The migration aptitudes of polycyclic bridgehead groups, cycloalkyl groups as well as of β-, γ- and δ-branched alkyl groups in the Chapman variant of the Beckmann rearrangement were determined.From these data it is concluded that at transition state 2 the migrating group is not resembling a planarised carbenium ion R+, but rather a pentacoordinated carbonium ion structure.Because only small geometrical changes occur in the migrating group vertical stabilisation of charge at transition state is believed to have significant influence on the migration aptitudes.
- Langhals, Heinz,Ruechardt, Christoph
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p. 3831 - 3854
(2007/10/02)
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