Ethylene Aldehyde

The scope of the reaction has been successfully extended to a,p-ethylenic aldehydes,5 esters,6 and amides7 as well as to a,p-acetylenic ketones8 (see Table IV). With esters, the reaction must be performed in the presence of chlorotrimethylsilane (MeaSiCI) to avoid the Claisen reaction by trapping the intermediate enolate. In most cases the organomanganese procedure is simple and more efficient than the organocopper procedure. 

Synonyms Acraldehyde Acrylaldehyde /rans-Acrolein Acrylic aldehyde AI3-24160 Allyl aldehyde Aqualin Aqualine Biocide BRN 1701567 Caswell No. 009 CCRIS 3278 Crolean EINECS 203-453-4 Ethylene aldehyde Magnacide Magnacide H NSC 8819 Papite Propenal 2-Propenal Prop-2-en-l-al 2-Propen-l-one Propylene aldehyde RCRA waste number P003 Slimicide UN 1092. 

Ethyl sec-amyl ketone, see 5-Methyl-3-heptanone Ethylbenzol, see Ethylbenzene Ethyl butyl ketone, see 3-Heptanone Ethyl n-butyl ketone, see 3-Heptanone Ethyl carbinol, see 1-Propanol Ethyl cellosolve, see 2-Ethoxyethanol Ethyl chloride, see Chloroethane Ethylcyclopentan, see Ethylcyclopentane Ethyldimethylmethane, see 2-Methylbutane Ethylendiamine, see Ethylenediamine Ethylene aldehyde, see Acrolein Ethylene bromide, see Ethylene dibromide Ethylene bromide glycol dibromide, see Ethylene dibromide... 

Another general method for the preparation of 19,19,19- and 20,20,20-trifluor-oretinals involves the aldol condensation of trifluoroacetone with an ethylenic aldehyde. When performed in the presence of acetic acid and piperidine, it affords an a, S-unsaturated ketone. Applied to cyclocitral and its homologues, the method leads to polyenic trifluoromethyl ketones. From these ketones, the various tri-fluorinated retinoids are prepared by known methods (Figure 4.24). ... 

Ethylene Aldehyde. See Acrolein A96-L Ethylenecarboxylic Acid. See Acrylic Acid A96-R... 

In conctwilon, the two pathways of our umpolung method can be satisfactorily applied to the a,p ethylenic aldehydes or ketones bearing no substituent or an alkyl at the vinylic carbon p to the carbonyl group but, when an aryl group substitutes this position, only the second pathway is possible with some reactive aldehydes. 

Synonyms and trade names acrylic aldehyde, acraldehyde, allyl aldehyde, ethylene aldehyde... 

SYNS ACQUINITE ACRALDEHYDE ACROLEINA (ITALIAN) ACROLEINE pUTCH, FRENCH) ACRYLALDEHYD (GERMAN) ACRYLALDEHYDE ACRYLIC ALDEHYDE AKROLEIN (CZECH) AKROLEINA (POLISH) ALDEHYDE ACRYLIQUE (FRENCH) ALDEIDE ACRILICA (ITALIAN) ALLYL ALDEHYDE AQUAUNE BIOCIDE CROLEAN ETHYLENE ALDEHYDE MAGNACIDE H NSC-8819 ... 

This sequence transforms acyclic ketones and aldehydes into a-methylene ketones and a-methyl-a,)5-unsaturated ketones and aldehydes It has been illustrated by the synthesis of eucarvone, ( )-nuciferal and ( )-manicone This ring-opening of chlorosiloxycyc-lopropanes with ClSiMea elimination appears to be a practical route to Z or a,)5-ethylenic aldehydes and ketones depending on the stereochemistry of the reactants. For example, conversion in MeOH-NEta at 20°C of the 2-chloro-2-methyl-3-pentyl-l-trimethylsiloxycyclopropanes (derived from the addition of the chloromethylcarbene to the E and Z silyl enol ethers of n-heptanal) leads either to or Z 2-methyl-oct-2-enal (equation 65). ... 

With 3c,j -ethylenic aldehydes and ketones, the balance between 1,2- and 1,4-addition is particularly sensitive to the following factors ... 

Synonyms Acrylaldehyde Acrylic aldehyde Allyl aldehyde Aqualin Ethylene aldehyde 2-Propenal... 

Reduction of a,p-ethylenic aldehydes and ketones can lead to three compounds (Figure 3.79) ... 

The reason for the lack of follow-up on this synthetic route may be attributed to literature reports of failures to isolate or even observe the expected dihydropyrimidines, particularly in the case of the simple a,/ -ethylenic aldehydes.143,146 Dihydropyrimidine formation from a,/ -unsat-urated carbonyl compounds and amidines occurs via nucleophilic attack by amidine at the activated double bond (Michael-type addition), followed by ring closure and dehydration (see Scheme 4). In the course of confirming this reaction scheme, the intermediacy of tetrahydropyrimidines and dihydropyrimidines was demonstrated. 

Oxo compounds from halides via nitrones a,/5-Ethylene aldehydes... 

Aldehydocarboxylic acid esters from a,/ -ethylene aldehydes... 

ETHYLENE ALDEHYDE (107-02-8) CHj=CHCHO Highly flammable liquid extremely low ignition temperature makes it very dangerous. Forms explosive mixture with air [explosion limits in air (vol %) 2.8 to 31 flash point -15°F/-26°C autoignition tenq) 453°F/234°C Fire Rating 3]. Unstable and very reactive. In storage, over time, it can form heat- and shock-sensitive... 

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