The olefinic double bonds in the cyclic ene-amines (5) and (8) have been shown to have the cis-configuration since two conformational diastereoisomers are formed in each case on quaternisation at nitrogen. The eleven-membered ring ene-amine (5). which is conformationally stable on the 1H n.m.r. time-scale up to +160 °C, undergoes transannular reactions involving the carbon-carbon double bond and the nitrogen atom in acidic, neutral, and basic media. Although the nine-membered ring ene-amine (8). which is conformationally mobile on the 1H n.m.r. time-scale at room temperature, also undergoes transannular reactions involving the carbon-carbon double bond and the nitrogen atom in acidic and neutral media, more vigorous reaction conditions are required.
|Original language||English (US)|
|Number of pages||6|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|State||Published - 1978|
ASJC Scopus subject areas