2536-34-7Relevant academic research and scientific papers
A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions
Huy, Peter H.,Filbrich, Isabel
supporting information, p. 7410 - 7416 (2018/04/30)
A general formamide-catalyzed protocol for the efficient transformation of alcohols into alkyl chlorides, which is promoted by substoichiometric amounts (down to 34 mol %) of inexpensive trichlorotriazine (TCT), is introduced. This is the first example of a TCT-mediated dihydroxychlorination of an OH-containing substrate (e.g., alcohols and carboxylic acids) in which all three chlorine atoms of TCT are transferred to the starting material. The consequently enhanced atom economy facilitates a significantly improved waste balance (E-factors down to 4), cost efficiency, and scalability (>50 g). Furthermore, the current procedure is distinguished by high levels of functional-group compatibility and stereoselectivity, as only weakly acidic cyanuric acid is released as exclusive byproduct. Finally, a one-pot protocol for the preparation of amines, azides, ethers, and sulfides enabled the synthesis of the drug rivastigmine with twofold SN2 inversion, which demonstrates the high practical value of the presented method.
Preparation and some reactions of ω-chloro derivatives from aleuritic acid and related compounds
Subramanian,Passey, Sarita
, p. 23 - 27 (2007/10/03)
Synthesis of ω-chloro compounds obtained from aleuritic acid and its derivatives have been carried out and the known triphenylphosphine-carbon tetrachloride procedure has been found to be the most suitable for this purpose. The C-Cl bond has been found to be sufficiently reactive towards a Wittig reaction, dilithium tetrachlorocuprate catalyzed alkylation and macrocyclization, indicating the usefulness of the chloro compounds.
