Allyl aldehyde

Allyl vinyl ethers have been prepared using the ylide (101) but only from non-enolizable carbonyl compounds. The ethers rearrange on heating to give a-allyl aldehydes, e.g. (102). 

Among phosphonate esters (170) used in olefin synthesis were those with R = S-CeHi-Br-/ , S02 C6H4-Br-A CO-NHR, and S CHa CEi-XHa. The allyl vinyl thio-ethers (171) obtained using the last of these gave a-allyl-aldehydes on pyrolysis in the presence of red mercuric oxide. 

Hg. Allylmercury bromide and diallylmercury are both stable in water. They can allylate aldehydes in aqueous media but, in the case of allylmercury bromide, activation with tetrahexylammonium bromide was necessary.186 The allylation reaction is chemoselective towards aldehyde on the contrary, ketone compounds are unaffected. 

Acrolein Allyl aldehyde, propenal) CH2 CHCHO -26 278 2.8-31.0 0.8 1.9 53 Colourless/yellow liquid Pungent unpleasant odour Water soluble Irritant Can polymerize exothermically with strong alkalis, heat or light Can form peroxides... 

CAS Number Acraldehyde Acrolein Acryladehyde Acrylaldehyde Acrylic aldehyde Allyl aldehyde Aqualin Aquilin, Magnacide H Propenal 107-02-8... 

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. 

Synonyms Acrylaldehyde 2-propenal allyl aldehyde propylene aldehyde Aqualin... 

ACROLEIN Acraldehyde, Acrylic Aldehyde, Allyl Aldehyde, Ethylene Aidehide, 2-Propenal, Acrylaldehyde Flammable Liquid, III 3 3 2 ... 

The enzyme found in the liver will deaminate secondary and tertiary aliphatic amines as well as primary amines, although the latter are the preferred substrates and are deaminated faster. Secondary and tertiary amines are preferentially dealky la ted to primary amines. For aromatic amines, such as benzylamine, electron-withdrawing substituents on the ring will increase the reaction rate. The product of the reaction is an aldehyde (Fig. 4.30). Amines such as amphetamine are not substrates, seemingly due to the presence of a methyl group on the a-carbon atom (Fig. 4.27). Monoamine oxidase is important in the metabolic activation and subsequent toxicity of allylamine (Fig. 4.31), which is highly toxic to the heart. The presence of the amine oxidase in heart tissue allows metabolism to the toxic metabolite, allyl aldehyde (Fig. 4.31). Another example is the metabolism of MPTP to a toxic metabolite by monoamine oxidase in the central nervous system, which is discussed in more detail in chapter 7. 

Allylation conditions are similar to those used for benzylation to a certain extent. Williamson s etherification using allyl bromides and NaH smoothly produces the allyl ethers [85], NaH can be replaced with BaO when base-sensitive moieties are present in the molecule [86, 87], The use of allyl imidates or TMSOTf-catalyzed Et3SiH-reductive allylation of a TMS ether using allyl aldehydes also provides the... 

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 ... 

When allyl alcohol, Ai-propen-ol-3, is oxidized carefully allyl aldehyde is obtained. As this aldehyde yields acrylic acid on further oxidation it is more commonly known as acrylic aldehyde and also as acrolein. 

Because of the rare and unpredictable nature of hepatobihary reactions to terbinafine, the mechanism of hepatotoxicity has been hypothesized to be either immunological or metabolically mediated. A potentially toxic reactive metabolite of terbinafine, 7,7-dimethylhept-2-ene-4-jmal (TBF-A), the A-dealkylation product of terbinafine, has been identified in vitro (43). The authors speculated that this allylic aldehyde metabolite, formed by hver enzymes and conjugated with glutathione, would be transported across the canalicular membrane of hepatocytes and concentrated in the bile. The reactive monoglutathione conjugate could bind to hepatobiliary proteins and cause direct toxicity. Alternatively, it could modify canahcular proteins and lead to an immune-mediated reaction, causing cholestatic dysfunction. 

Aromatic and allylic aldehydes are converted into amides by oxidation at —20° with nickel peroxide in the presence of ammonia. At higher temperatures nitriles are formed. 

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