Difunctional Carbonyl Compounds

A. ­ 1,3 & 1,5-Dicarbonyl chemistry

I. Malonates & 1,3-dicarbonyl compounds

i) Introduction

ii) Alkylation

iii) Control Groups

iv) Knovenagel Reaction

v) Other Decarboxylation Methods

vi) Advanced Dicarbonyl reactions ­ dianions

II. Enones

i) Synthesis

ii) Reactivity 1,2 vs. 1,4

iii) Cuprates

iv) Michael acceptors

v) Li metal

III. 1,5-Dicarbonyl relationship

i) From conjugate addition

ii) Reactions with enamines and silyl enol ethers

iii) Robinson annelation Perkin reaction

iv) More Michael acceptors

v) Advanced Conjugate additions (leaving group on the beta-position)

B.­ 1,n-Dicarbonyl chemistry

I. 1,4-Dicarbonyl relationship

i) a-Halocarbonyls

ii) Epoxides

iii) Nitro compounds

iv) Reactions of 1,4-dicarbonyls

II. 1,2-Dicarbonyl relationship

i) Benzoin reaction

ii) Acyloin reaction

iii) Ozonolysis

iv) Pinacol

III. 1,6-Dicarbonyls

i) Ozonolysis

C. ­ Miscellaneous

I. Advanced enones

i) Claisen for g,d enones

ii) Synthesis of a,b,g,d unsaturated carbonyls

II. Darzens reaction