propanal to oxalic acid
Answers
Answer:
Propionaldehyde t-Butylimine1
(R = t-Bu)
[7020-81-7] · C7H15N · Propionaldehyde t-Butylimine · (MW 113.23) (R = t-Bu, Li salt)
[75261-61-9] · C7H14LiN · 2-Lithiopropionaldehyde t-Butylimine · (MW 119.16) (R = Cy)
[6898-80-2] · C9H17N · Propionaldehyde Cyclohexylimine · (MW 139.27)
(two-carbon nucleophile in enolate alkylations, conjugate addition reactions, and directed aldol condensations; especially useful for a-monoalkylations and three-carbon homologations1)
Physical Data: R = t-Bu: bp 103 °C,2 48-50 °C/115 mmHg,3 47-49 °C/95 mmHg.4 R = Cy: bp 63-64 °C/15 mmHg,4 62-63 °C/12 mmHg;5 n16D 1.4450.
Solubility: sol THF, ether, CCl4, pentane, benzene, toluene.
Form Supplied in: colorless liquid when freshly distilled; darkens on prolonged standing
Analysis of Reagent Purity: NMR or IR.
Preparative Methods: the general method adapted by Stork and Dowd from the procedure developed earlier by Tiollais is said to be highly efficient for the synthesis of aldimines from low-boiling aldehydes.2 Quantitative yields have also been reported when propanal is added to a preformed amine-Titanium(IV) Chloride complex.6 Lithiopropionaldehyde t-butylimine is usually prepared by reaction with a slight excess of a hindered nonnucleophilic base like Lithium Diethylamide in THF or ether at -78 °C under N2 or argon.7,8 A variation of this method calls for addition of Hexamethylphosphoric Triamide to the reaction mixture.8b
Handling, Storage, and Precautions: best used when freshly prepared. Imines can be distilled, but they tend to polymerize upon long standing. Stored samples are distilled over KOH to remove high-boiling condensation products prior to use. Storage as neat liquids is not recommended for long periods, but solutions in dry THF (0.4 M) can be stored at -20 to -30 °C with minimal deterioration.9 In acidic solutions, the imine reverts to propanal and the amine. The lithiated imine is generally prepared in situ under N2 or argon. Use in a fume hood.
Condensation Reactions.
The synthetic value of these reagents lies in their facile conversion to imine anions and their low propensity for self-aldol condensation. These characteristics favor their use over propionaldehyde in directed crossed-aldol condensation reactions. (E)-a,b-Unsaturated aldehydes are stereoselectively formed upon hydrolysis and dehydration of the a-methyl-b-hydroxy aldehyde adducts. This strategy is illustrated in the synthesis of nuciferal (eq 1) and sinensal,7 and in a variety of intermediates for the synthesis of natural products,1,10
These reagents can tolerate the presence of other functional groups in the electrophile (eq 2).10 Phosphonates11 and trialkylsilyl groups3,8,12 have been used to stabilize the lithio imine anions in these reactions.
g-Diketones have been prepared by Michael-type additions of the t-Bu imine anion and by alkylation with allylic halides followed by ozonolysis.1
HELLO MATE HERE IS YOUR ANSWER
propanal in acid is propanoic acid.
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