A Simple Synthesis of 1-Aminohexa-1,3,5-trienes - the Formation of Stable Conjugated Primary Enamines Under Thermodynamic Control

Michael Riedel; Gerhard Erker

doi:10.1055/s-1994-25634

Synthesis 1994; 1994(10): 1039-1042
DOI: 10.1055/s-1994-25634

paper

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A Simple Synthesis of 1-Aminohexa-1,3,5-trienes - the Formation of Stable Conjugated Primary Enamines Under Thermodynamic Control

Michael Riedel^* , Gerhard Erker

^*Organisch-Chemisches Institut der Universität Münster, Corrensstraße 40, D-48149 Münster, Germany

Abstract

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Pentadienyllithium reacts with nitriles R-CN (R = 2-pyridyl, phenyl, p-tolyl, 2-furyl, 2-thienyl, tert-butyl) to yield the metallated 1-substituted trienamine systems 7a-f (a mixture of 1Z,3E)/(1E,3E)-isomers). Controlled hydrolysis with aqueous ammonia gave the corresponding 1-aminohexa-1,3,5-triene systems 8a-f as a (1Z,3Z)/(1E,3E)-mixture of isomers in 75-85% overall yield. Under thermodynamic control the conjugated primary enamines are much preferred over their ketimine tautomers which could not be detected by ¹H NMR spectroscopy at equilibrium conditions.

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