ABSTRACT

I I I . Framework Structure 27 A . Thermochemistry and Isomerization 27 B . Enamines o f Cyclic Ketones 34 C. Enamines o f Acyclic Ketones and Aldehydes 54

IV . Physical Properties o f Enamines 60 A . Infrared Spectra 60 B . Ultraviolet Spectra 66 C. Nuclear Magnetic Resonance Spectra 66 D. Mass Spectra 74 E. Basicity 77 References 83

The term ’’enamine” was first introduced by Wittig and Blumenthal [1] as the nitrogen analog of the term ” enol.” Enamine chemistry was the subject o f study by Mannich and Davidsen [2] in 1936, but it was the

\ \ / oH / c = = c \ / c = c \

enamine enol

pioneering work o f Stork and his co-workers [3,148] that strikinglybrought it to the attention o f the organic chemistry world.