25023-01-2Relevant articles and documents
Chlorination process, alkylation of products of said process and some products thereof
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, (2008/06/13)
Compounds having acidic protons and a molecular structure which can delocalize the electron density of the conjugate base (target compounds) are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is an tetraalkylammonium hydroxide. Chlorinated products, preferably gem-dichloro compounds, are produced. The gem-dichloro compounds are useful for alkylation of aromatic compounds. For instance fluorene is chlorinated to form 9,9-dichlorofluorene which is reacted with such compounds as phenol or aniline to form such compounds as 9,9-bis(hydroxyphenyl)fluorene, 9,9-bis(aminophenyl)fluorene, or 9-aminophenyl-9-chlorofluorene.
Hexamethylphosphoramide Catalyzed Conversion of Carbonyl Compounds into geminal-Dichlorides with Thionyl Chloride
Khurana, J. M.,Mehta, Sanjay
, p. 1128 (2007/10/02)
α, β-Unsaturated and aromatic aldehydes can be converted into geminal-dichlorides quantitatively by reaction with thionyl chloride in the presence of catalytic amounts of hexamethylphosphoramide at room temperature
Diaryldichlorocarbonyl Ylides Derived from Dichlorocarbene and Aromatic Ketones
Martin, Charles W.,Gill, Harpal S.,Landgrebe, John A.
, p. 1898 - 1901 (2007/10/02)
The thermal decomposition of phenyl(bromodichloromethyl)mercury (4) in the presence of benzophenone (2) in dry benzene at 80 degC resulted in α-chlorodiphenylacetyl chloride (6) as the only major initial product together with small amounts of dichlorodiphenylmethane (5) and carbon monoxide.Analogous products were observed from fluorenone (3).Dimethyl acetylenedicarboxylate (15) failed to trap the presumed intermediate dihalocarbonyl ylide from either ketone.Attempts to explain the difference in behavior between dihalocarbonyl ylides derived from benzaldehydes and diaryl ketones suggest that in the latter case a twist in the plane of the ylide caused by endo,endo interactions of a chlorine and an aromatic ring leads to rapid closure to oxirane 11 followed by rearrangement to acid chloride 6.Alternative explanations are also explored.