B. Pugin, L. Venanzi
Jun 30, 1981
Citations
0
Influential Citations
22
Citations
Journal
Journal of Organometallic Chemistry
Abstract
Abstract The trifluoromethanesulphonate salts of the aminoalkenes CH2CH(CH2)3-NH2, its 2-methyl, 2,2-dimethyl and N-iso-propyl-derivatives, and CH2CH-(CH2)4NH2 cyclize in the presence of [PdCl2(PhCN)2] and a nitrogen base to produce the corresponding C- or N-substituted 2-methylpyrrolidines and 2-methylpiperidine. E-CH3CHCH(CH2)3NH2 produces 2-ethylpyrrolidine and a small amount of 2-methylpiperidine. The regio-selectivity of these reactions differs from that observed for the cyclization of the same substrates promoted by [PtCl4]2-: (1) the palladium reaction with 2-methylpent-4-enylamine produces ca. a 4 : 6 ratio of cis- and trans-2, 4-dimethylpyrrolidine while with platinum the converse is true; (2) there is a more marked tendency for attack of the amine at the more substituted alkene carbon atom in the palladium than in the platinum reactions.