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Organic Chemistry 2

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Coupling of Amine and 1,4-diketone

ORGO2-BGEB1U

The condensation of primary amines with 1,4-diketones does not afford the double imine. A further reaction process occurs due to the proximity of the two $C=O$ groups to produce a much more stable structure.

What is the product of the following reaction?

Spectral data for the product has been provided. Note that no skeletal rearrangements occur in this reaction.

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$^1H$ $NMR$: 7.3-7.1 (5H, multiplet), 6.0 (2H, singlet), 5.5 (2H, singlet), 2.2 (6H, singlet).

$^{13}C$ $NMR$: 138, 129, 128, 127, 125, 106, 49, 13.

A

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B

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C

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D

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