79462-37-6

Upstream product

• 5171-99-3 (1-phenylpropan-2-ylidene)hydrazine 
• 105732-47-6 2-methyl-2-benzyl-1,3-benzodioxole 
• 26163-01-9 phenylacetone dimethylketal 
• 103-79-7 1-phenyl-acetone 
• 100-39-0 benzyl bromide 
• 71648-14-1 C₂H₃Br₂Li 

Downstream Products

• 637-50-3 1-phenylpropene 

Relevant academic research and scientific papers

Halogenative Deoxygenation of Ketones; Vinyl Bromides and/or gem-Dibromides by Cleavage of 1,3-Benzodioxoles (Ketone Phenylene Acetals) with Boron Tribromide

Representative ketones 1 have been converted in generally good yields to the respective 1,3-benzodioxoles 5 by trans-acetalization of ketone dimethyl acetals with 1,2-dihydroxybenzene, and cleaved with boron tribromide. 1,3-Benzodioxoles derived from α-unbranched aliphatic ketones gave in general a mixture of vinyl bromides and gem-dibromides; pure gem-dibromides could be selectively obtained in most of cases using a suitable reaction time. 1,3-Benzodioxoles derived from α-branched ketones gave complex mixtures and their cleavage appears to be of little synthetic signifance. 1,3-Benzodioxoles of aromatic ketones gave vinyl bromides only.Aliphatic cyclic gem-dibromides 3 were converted to the respective vinyl bromides 2 by phase-transfer-catalysed dehydrobromination.

Decomposition et proprietes electrophiles des carbenoides monohalogenes non fonctionnels

Geminal substitution of a carbon atom by a halogen atom and a lithium atom gives rise to electrophilic properties and great instability to the corresponding α-monohalogenoalkyllithium.From NMR data, it appears that the functional carbon atom exhibits an electron deficiency in connection with an intramolecular halogen-lithium coordination.This description is in agreement with the structure proposed for LiCH2F on the basis of "ab initio" calculations.Electronic and steric effects of the other substituents of the functional carbon atom and the influence of the reaction medium (basicity of solvents, Lewis acidity of associated salts) on the variation of electrophilic and nucleophilic behaviour and stability of carbenoids (mono, di, trihalogeno) can be rationalized on the basis of this metallocarbenium halogenide structure.