108229-10-3Relevant academic research and scientific papers
Naphthalene-catalysed lithiation of dialkyl sulfates: A new route for organolithium reagents
Guijarro,Mancheno,Yus
, p. 5597 - 5600 (1992)
The lithiation of primary and secondary dialkyl sulfates with an excess of lithium powder in the presence of a catalytic amount of naphthalene at -78°C leads to the corresponding alkyl-lithium reagents (1:2 molar ratio), which react with different electrophiles, mainly carbonyl compounds, to yield the expected coupling products. This methodology represents an indirect way for transforming alcohols into organolithium compounds through the corresponding dialkyl sulfates.
Palladium-Catalyzed isomerization of exo-methylenic allylic alcohols
Fordred, Paul S.,Niyadurupola, D.Gangani,Wisedale, Richard,Bull, Stevend
scheme or table, p. 2310 - 2314 (2009/12/27)
Treatment of allylic alcohols containing a 1,1-disubstituted alkene with a palladium catalyst and hydrogen gas (1 bar) results in facile isomerization to their corresponding trisubstituted (E)-allylic alcohols, along with small amounts of the corresponding hydrogenated products.
Synthesis of Organolithium Compounds from Phenyl Selenides
Krief, Alain,Nazih, Abdesslame,Hobe, Myriam
, p. 8111 - 8114 (2007/10/02)
Alkyl aryl selenides react with lithium arenides to produce, regioselectively, alkyllithiums and lithium arylselenolates.Experimental conditions, especially the temperature, have a profound effect on the course of this reaction and on the nature of the products.
Direct transformation of dialkyl sulfates into alkyllithium reagents by a naphthalene-catalysed lithiation
Guijarro, David,Guillena, Gabricia,Mancheno, Balbino,Yus, Miguel
, p. 3427 - 3436 (2007/10/02)
The lithiation of primary and secondary dialkyl sufates with an excess of lithium powder in the presence of a catalytic amount of naphthalene (4 mol %) in THF at -78°C leads to the corresponding alkyllithium reagents (1:2 molar ratio) which react with different electrophiles, mainly carbonyl compounds, to yield after hydrolysis, the expected coupling products. This methodology represents an indirect way to transform alcohols into organolithium compounds through the corresponding dialkyl sulfates. When the same procedure is applied to five or six member cyclic sulfates (derived from 1,2- or 1,3-diols) only products arising from a β- or γ-elimination process (giving olefins or cyclopropanes), respectively, are obtained.
AZO ANIONS IN SYNTHESIS. USE OF TRITYL- AND DIPHENYL-4-PYRIDYLMETHYLHYDRAZONES FOR REDUCTIVE C-C BOND FORMATION.
Baldwin, Jack E.,Adlington, Robert M.,Bottaro, Jeffrey C.,Kolhe, Jayant N.,Newington, Ian M.,Perry, Matthew W. D.
, p. 4235 - 4246 (2007/10/02)
The lithium salts of trityl- and diphenyl-4-pyridylmethyl-hydrazones of both aldehydes and ketones react with electrophiles (alkyl halides, aldehydes, ketones, crotonates) at low temperature to form C-trapped azo compounds; these intermediates decompose homolytically with loss of nitrogen below room temperature and can be diverted in a synthetically useful way to alkanes, alkenes, alcohols or saturated esters.
