88-66-4Relevant academic research and scientific papers
One-pot, oxidative and selective conversion of benzylic silyl and tetrahydropyranyl ethers to gem-dichlorides using trichloroisocyanuric acid and triphenylphosphine as an efficient and neutral system
Khadem Moghaddam, Roqayeh,Aghapour, Ghasem
, p. 398 - 406 (2020/11/19)
A one-pot and oxidative method is described for the first time for the conversion of benzylic trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers to gem-dichlorides using trichloroisocyanuric acid (TCCA) and triphenylphosphine (PPh3) in neutral media. Various theses substrates containing electron withdrawing or donating groups can be efficiently converted to their corresponding gem-dichlorides in good to excellent yields. The present method shows a high degree of chemoselectivity, and due to its one-pot nature is in accordance with green chemistry.
Formamide Catalysis Facilitates the Transformation of Aldehydes into Geminal Dichlorides
Huy, Peter Helmut
supporting information, p. 2474 - 2483 (2019/06/08)
Herein, a novel method for the transformation of aldehydes into geminal dichlorides based on phthaloyl chloride as reagent and N -formylpyrrolidine as Lewis base catalyst is disclosed. Given the mild reaction conditions, the current protocol is distinguished by high levels of functional group compatibility and scalability and is operationally simple. The in situ formation of a Vilsmeier Haack reagent type intermediate is likely to be essential for this organocatalytic nucleophilic substitution reaction.
One-pot, selective and mild conversion of benzylic alcohols to gem -dichlorides using chlorodiphenylphosphine and 2,3-dichloro-5,6-dicyanobenzoquinone as a new and neutral system
Aghapour, Ghasem,Mohamadian, Samaneh
, p. 520 - 527 (2015/05/20)
A mild and one-pot conversion of benzylic alcohols to their corresponding gem-dichlorides is reported for the first time using chlorodiphenylphosphine (ClPPh2) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in dichloromethane under neutral conditions and at room temperature. The present method can be efficiently used for preparation of gem-dichlorides even in the presence of some other functional groups with excellent chemoselectivity.
Facile conversion of aldehydes and ketones to gem-dichlorides using chlorodiphenylphosphine/N-chlorosuccinimide as a new and neutral system
Aghapour, Ghasem,Afzali, Asieh
experimental part, p. 4023 - 4035 (2009/04/11)
Aldehydes and ketones are easily converted to their corresponding gem-dichlorides using a mixture of chlorodiphenylphosphine and N-chlorosuccinimide (ClPPh2/NCS) in dichloromethane under neutral conditions and at room temperature. Copyright Taylor & Francis Group, LLC.
Conversion of aromatic aldehydes to gem-dichlorides using boron trichloride. A new highly efficient method for preparing dichloroarylmethanes
Kabalka, George W.,Wu, Zhongzhi
, p. 579 - 581 (2007/10/03)
The chlorination of aromatic aldehydes with boron trichloride in hexane under reflux conditions produces the corresponding dichloromethyl derivatives in excellent yields. (C) 2000 Elsevier Science Ltd.
A simple and efficient procedure for the preparation of benzal chlorides and benzal bromides
Léonel, Eric,Paugam, Jean-Paul,Heintz, Monique,Nédélec, Jean-Yves
, p. 4015 - 4024 (2007/10/03)
Benzal chlorides and benzal bromides were conveniently synthesized by reaction of aryl aldehydes with a Vilsmeier type reagent formed in situ by reduction of CCl4 or CBr4 in dimethylformamide (DMF) as solvent.
New applications of tungsten hexachloride (WCl6) in organic synthesis. Halo-de-hydroxylation and dihalo-de-oxo-bisubstitution reactions
Firouzabadi, Habib,Shiriny, Farhad
, p. 14929 - 14936 (2007/10/03)
Tungsten hexachloride (WCl6) has been used for the halo-de-hydroxylation and dihalo-de-oxo-bisubstitution reactions of benzylic alcohols, benzaldehydes, acyloins, and epoxides to their chlorides, gem-dichlorides, vic-trichlorides, and vic-dichlorides respectively.
