55106-21-3

Basic information

• Product Name: Benzeneacetaldehyde, a-(1-methylethylidene)-
• CAS NO: 55106-21-3
• Molecular Formula: C11H12O
• Molecular Weight: 160.216
• Mol File: 55106-21-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzeneacetaldehyde, a-(1-methylethylidene)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetaldehyde, a-(1-methylethylidene)-(55106-21-3)
• EPA Substance Registry System: Benzeneacetaldehyde, a-(1-methylethylidene)-(55106-21-3)

Safety Data

• Hazardous Substances Data: 55106-21-3(Hazardous Substances Data)

Upstream product

• 21663-36-5 1-Phenyl-3-methyl-but-3-en-1,2-diol 
• 2591-86-8 N-Formylpiperidine 
• 109-72-8 n-butyllithium 
• 5912-93-6 1-bromo-2-methyl-1-phenyl-1-propene 
• 140-29-4 phenylacetonitrile 
• 51631-26-6 α-isopropyl-α-phenylacetyl chloride 
• 3508-94-9 3-methyl-2-phenylbutyric acid 
• 2439-44-3 3-methyl-2-phenylbutanal 
• 5558-29-2 3-methyl-2-phenyl-butyronitrile 
• 33131-36-1 methyl 3-methyl-2-phenylbut-2-enoate 
• 108-86-1 bromobenzene 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 55106-23-5 2-chloro-3-methyl-2-phenylbutanal 
• 55106-18-8 Brom-1-methyl-3-phenyl-3-epoxy-1,2-butan 

Downstream Products

• 162292-18-4 2-Methyl-3-phenyl-2-hepten-5-yn-4-one 
• 162292-72-0 2-Methyl-3-phenyl-hept-2-en-5-yn-4-ol 

Relevant articles and documents

Heck Arylation of α,β-Unsaturated Aldehydes

The Heck arylation of α,β-unsaturated aldehydes is strongly dependent on the catalyst, the solvent and the base. Optimized conditions yielded either selectively cinnamyl derivatives (83%) or double arylation products (88% based on aryl conversion). A new α-arylation of β,β-disubstituted acrolein is also realized.

Stereochemistry of Carbenic 1,2-Vinyl Shifts

Various 1-phenylbut-3-enylidenes, (Ph)CCR2CH=CHR', were generated thermally and photolytically from tosylhydrazone (diazo) precursors. 1,2-Vinyl shifts, leading to 1,3-dienes, R′CH=CHC(Ph)=CR2, were found to predominate over γ-C-H insertion (R = Me) and to compete with 1,2-H shifts (R = H). Intramolecular addition to the double bond was detected in the case of R = R′ = Me. The resulting bicyclobutane is thermally stable and does not mediate the vinyl shift. Stereospecific migration of 1-propenyl groups (R′ = Me), with retention of configuration, was observed on thermolysis and direct photolysis of appropriate substrates. These data exclude the intervention of a triplet diradical and point to vinyl migration in the singlet manifold. Benzophenone-sensitized generation of the carbenes led to partial stereomutation but did not provide conclusive evidence for a triplet rearrangement (isomerization of the diene products could not be avoided under these conditions).