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- Title
Eisenpentacarbonyl-induzierte Reaktionen von Norbornadien und substituierten Olefinen.
- Authors
Schmid†, Hans; Naab, Paul; Hayakawa, Kenji
- Abstract
Iron Pentacarbonyl Induced Reactions of Norbornadiene and Substituted Olefins The photochemical reaction of norbornadiene and α, β-unsaturated nitriles, esters and amides in the presence of Fe(CO)5 was studied. Nitriles furnished the dinorbornenyl ketones 2a-c ( Scheme 1). Esters led to an addition of a norbornene moiety to the double bond giving the substituted α, β-unsaturated esters 10a and 10b ( Scheme 5). Methacrylamide and methyl β-aminocrotonate gave the cyclopentanone derivatives 14 and 17, respectively ( Schemes 7 and 8). The reaction was in all cases highly stereoselective with general exo-substitution on the norbornadiene. The attack on the unsymmetric olefins occurred regiospecifically at that point of the double bond which was furthest away from the functional group. A plausible mechanism for these reactions is suggested in Schemes 10 and 11.
- Publication
Helvetica Chimica Acta, 1978, Vol 61, Issue 4, p1427
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19780610427