Novel 1,2-diaza-1,5,9-cyclo dodecatrienes and 1,2-diaza-1-cyclododecenes
AssigneeCiba-Geigy Corporation
InventorsBernard Hugelin, Eduard Troxler
Life of this patent
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Abstract
New unsaturated 1,2-diazacyclododecanes, more particularly 1,2-diazacyclododecatrienes-1,5,9 and 1,2-diazacyclododecanes-1 and a novel process for the preparation thereof are disclosed which process comprises reacting a 1,3-diolefin with an azine in the presence of certain nickel catalysts. Said process unexpectedly yields 12-membered ring compounds only, and more especially oligomerization products of 2 mols of a 1,3-diolefin and 1 mol of an azine, while deactivation of the nickel catalyst by the -N=N-bond is avoided.
Claims15
A 1,2-diaza-1,5,9-cyclododecatriene or 1,2-diaza-1-cyclododecene of the formula ##EQU4## wherein R.sub.1 and R.sub.1 ' independently of one another denote alkyl of one to six carbon atoms;
- alkenyl of up to four carbon atoms;
- alkyl of one to four carbon atoms substituted by phenyl;
- alkenyl of up to four carbon atoms substituted by phenyl;
- cyclohexyl;
- phenyl;
- phenyl substituted in the 4-position by a halogen atom, an alkyl of one to four carbon atoms or an alkoxy of one to four carbon atoms;
- 1-naphthyl;
- or 3,4-methylenedioxyphenyl;
- R.sub.2 and R.sub.2 ' independently of one another denote hydrogen;
- alkyl of one to four carbon atoms;
- or
- R.sub.1 and R.sub.2, or R.sub.1 ' and R.sub.2 ', together with the carbon atoms to which they are bonded form a cycloalkyl ring of five to 12 carbon atoms.
A compound according to claim 1, 3,12-diethyl-1,2-diaza-1,5,9-cyclododecatriene.
A compound according to claim 1, 3,12-diphenyl-1,2-diaza-1,5,9-cyclododecatriene.
A compound according to claim 1, 3,12-di(4-methoxyphenyl)-1,2-diaza-1,5,9-cyclododecatriene.
A compound according to claim 1, 3,3,12,12-tetramethyl-1,2-diaza-1,5,9-cyclododecatriene.
A compound according to claim 1, 3,12-diphenyl-1,2-diaza-1-cyclododecene.
Dependencies are inferred from the claim text.