Method for preparing cyclopropylamines

A process for preparing cyclopropylamines of the formula ##STR10## wherein R.sup.1 represents hydrogen, optionally substituted C.sub.1 -C.sub.6 -alkyl, optionally substituted C.sub.2 -C.sub.6 -alkenyl, optionally substituted C.sub.3 -C.sub.7 -cycloalk(en)yl, optionally substituted C.sub.6 -C.sub.10 -aryl, or optionally substituted C.sub.7 -C.sub.12 -aralkyl,

• R.sup.2 and R.sup.3 independently of one another each represent optionally substituted C.sub.1 -C.sub.6 -alkyl, optionally substituted C.sub.2 -C.sub.6 -alkenyl, optionally substituted C.sub.5 -C.sub.7 -cycloalk(en)yl, optionally substituted C.sub.6 -C.sub.10 -aryl, or optionally substituted C.sub.7 -C.sub.12 -aralkyl,
• R.sup.4 and R.sup.5 either independently of one another and independently of R.sup.1 are each defined as R.sup.1, where R.sup.4 may additionally also represent N(H)(C.sub.1 -C.sub.6 -akyl) or O--C.sub.1 -C.sub.8 -alkyl, or R.sup.4 and R.sup.5 together represent a bridge of one of the formulae (II) to (V) ##STR11## wherein m represents an integer from 2 to 5 and
• n and p or p' independently of one another each represent zero or an integer from 1 to 4, where the sum of n+p is at least 2 and at most 6 and the sum n+p' is at least 1 and at most 4,
• R.sup.6 independently of R.sup.1 is as defined for R.sup.1, where R.sup.5 and R.sup.6 together may also represent --CH.sub.2 --CH.sub.2 --, and
• R .sup.7 represents optionally substituted C.sub.1 -C.sub.6 -alkyl, optionally substituted C.sub.2 -C.sub.6 -alkenyl, optionally substituted C.sub.3 -C.sub.7 -cycloalk(en)yl, optionally substituted C.sub.6 -C.sub.10 -aryl, or optionally substituted C.sub.7 -C.sub.12 -aralkyl, and
• where in the formula (IV) independently of one another 1 to 2 CH.sub.2 groups may optionally be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.7 -cycloalk(en)yl, C.sub.6 -C.sub.10 -aryl, or C.sub.7 -C.sub.12 -aralkyl,
• comprising reacting
• (1) a carboxamide of the formula ##STR12## wherein R.sup.1, R.sup.2, and R.sup.3 are each as defined for formula (I),
• with
• (2) an olefin of the formula ##STR13## wherein R.sup.4, R.sup.5, and R.sup.6 are each as defined for formula (I),
• (3) alkylmagnesium halides or zinc alkyl compounds of the formula
• R.sup.8 --X (VIII),
• wherein
• R.sup.8 represents straight-chain or branched C.sub.1 -C.sub.6 -alkyl or C.sub.5 -C.sub.7 -cycloalkyl, and
• X represents MgCl, MgBr, Mgl, ZnCl, ZnBr, Znl, or ZnR.sup.8, and
• (4) orthometallates of the formula (IX) ##STR14## wherein R.sup.9 represents straight-chain or branched C.sub.1 -C.sub.6 -alkyl, or C.sub.5 -C.sub.7 -cycloalkyl, or C.sub.6 -C.sub.10 -aryl,
• Y represents Ti, Zr, or V.dbd.O, and
• Z represents chlorine, bromine, or C.sub.1 -C.sub.4 -alkyl,
• with the provisos that when Y is Ti or Zr, then q represents 3 or 4 and r represents zero or 1 and the sum q+r=4, and that when Y is V.dbd.O, then q represents 3 and r represents zero.