97663-67-7Relevant academic research and scientific papers
REGIOSELEKTIVE CYCLOADDITIONEN VON METHYLENCYCLOPROPAN MIT ELEKTRONENARMEN OLEFINEN AN R3P-NICKEL(O)-KATALYSATOREN.
Binger, Paul,Wedemann, Petra
, p. 1045 - 1048 (1985)
The triorganyl-phosphane/-phosphite-Ni(O) catalyzed cycloaddition of methylenecyclopropane (1) with electron deficient alkenes leads regioselectively to 2,3- or 3,4-disubstituted methylenecyclopentanes depending on the electronic properties of the ol
Reactions of Methylenecyclopropanes, VII. Nickel(0)-catalysed Cycloadditions of Methylenecyclopropanes with Alkyl Acrylates
Binger, Paul,Brinkmann, Axel,Wedemann,Petra
, p. 2920 - 2930 (2007/10/02)
Cycloaddition reactions of methylenecyclopropane (1) and of the ring-methylated methylenecyclopropanes 5, 9, and 12 with alkyl acrylates are performed at nickel(0) catalysts, such as bis(1,5-cyclooctadiene)nickel under mild conditions (0 - 50 deg C).Depending on the degree of methylation of the three-membered ring, 1 and 5 give only alkyl 3-methylenecyclopentanecarboxylates (4 and 6), whereas 9 leads to a mixture of the methylenecyclopentane derivative 10 and the alkyl spirohexanecarboxylate 11, and 12 react to form only the spirohexane derivative 13.With 12 isomerisation to 2,3,3-trimethyl-1,4-pentadiene (15) also takes place.In the case of 9 the ratio of methylenecyclopentane to spirohexanecarboxylate can be influenced by the size of alkyl groups. - In the Ni0-catalysed reactions of 1 with substituted acrylates (methyl crotonate or diethyl maleate) codimerisation to 16 and 17 competes with cyclodimerisation to 2 and 3.
