Journal of Organic Chemistry p. 3867 - 3872 (1987)
Update date:2022-07-29
Topics:
Karczesy, J. J.
Arbogast, B.
Deinzer, M. L.
Pyrrolizidine alkaloid pyrrolws react rapidly with 4-(p-nitrobenzyl)pyridine under pseudo-first order conditions.A biexpotential first-order rate law is observed.Relative reactivities are grewatly influenced by the nature of the leaving group at C7. 2,3-Dihydro-1H-pyrrolizin-1-ol and dehydrosupinidine under pseudo-first-order reaction conditions obey a simple first-order rate expression.Evidence for oligomerization of the pyrrolizidine pyrrole nucleus has been obtained under these reaction conditions, and it is proposed that a second color-forming reaction sequence of nucleophile with the oligomer C9s accounts for the biexpotential rate law.
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