A 1,3-Sigmatropic Rearrangement Revealed in the Solid and Solution State Structures of a Chiral Sodium 1-Azaallyl Complex Derived from (S)-N-(α-Methylbenzyl)allylamine

The reaction of nBuNa with (S)-N-(α-methylbenzyl)allylamine, followed by the addition of tmeda, gives a chiral sodium 1-azaallyl complex, {[(S)-α-[PhC(H)MeN−··C(H)−··CHCH3)]Na·tmeda}2, as confirmed by single crystal X-ray diffraction and solution NMR spectroscopy, and is most likely the result of a 1,3-sigmatropic rearrangement and subsequent delocalisation within the resulting enamide. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)