Ketones historical perspective

From a historical perspective, the a-(dialkylamino)nitrile anions were the first acyl anion equivalents to undergo systematic investigation. More recent studies indicate that anions of a-(dialkylamino)nitriles derived from aliphatic, aromatic or heteroaromatic aldehydes intercept an array of electrophiles including alkyl halides, alkyl sulfonates, epoxides, aldehydes, ketones, acyl chlorides, chloroformates, unsaturated ketones, unsaturated esters and unsaturated nitriles. Aminonitriles are readily prepared and their anions are formed with a variety of bases such as sodium methoxide, KOH in alcohol, NaH, LDA, PhLi, sodium amide, 70% NaOH and potassium amide. Regeneration of the carbonyl group can be achieved... 

From a historic perspective, in 1936 Gilman and Straley (3) discovered that catalytic amounts of a copper salt lead to an increased reactivity of Grignard reagents. A little later, in 1941, Kharasch and Twaney (4) found that Grignard reagents react with a,/3-unsaturated ketones to afford products that result from... 

The only difference between this formulation and that of benzene is the historical view of benzene as a single molecule with two "main" overlapping resonance structures that were sufficiently similar that they could be coalesced into a single mental construct. On the other hand, the chemical difference between an alcohol and a ketone make such a viewpoint seem strange, if not completely untenable. Only because of the introduction of an extended bond set does such a perspective become viable. 

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