593-33-9

Usage

InChI:InChI=1/C14H29F/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h2-14H2,1H3

Upstream product

• 112-71-0 1-Bromotetradecane 
• 112-72-1 1-Tetradecanol 
• 6221-89-2 Trimethylsilyloxy-tetradecan 
• 72422-53-8 toluene-4-sulfonic acid tetradecyl ester 
• 88303-25-7 tetradecylmagnesium bromide 
• 77774-34-6 tetradecyl tert-butyldimethylsilyl ether 
• 19218-94-1 1-iodotetradecane 

Downstream Products

• 1120-36-1 1-tetradecene 

Relevant academic research and scientific papers

Deiodinative fluorination of alkyl iodide with p-iodotoluene difluoride

Oxidative fluorination of alkyl iodides with p-iodotoluene difluoride (4) was carried out. In the presence of Et3N-4HF, the fluorination reaction of prim-alkyl iodides selectively took place at the iodine position under mild conditions to give the corresponding alkyl fluorides in good yields.

Electrochemical fluorodeiodination of alkyl iodides

Electrochemical oxidation of alkyl iodides using Et3N-nHF complexes as an electrolyte proceeds under mild conditions to give alkyl fluorides in good yields. The reaction is highly chemoselective and the functional groups in the substrate such as an ester, ketone, chloride, and tosylate could be tolerated under the reaction conditions.

Fluorination of secondary and primary alcohols by thermal decomposition of electrochemically generated alkoxy triphenylphosphonium tetrafluoroborates

Replacement of hydroxyl groups in secondary and primary alcohols (1) with a fluorine atom arising from tetrafluoroborate anion has been performed by the electrochemical formation of alkoxy triphenylphosphonium tetrafluoroborates (2) from 1, followed by their thermal decomposition. The procedure is quite simple, involving: (1) constant-current electrolysis of a mixture of 1, Ph3P, and Ph3PH·BF4 in CH2Cl2 in an undivided cell; (2) refluxing a tetrahydrofuran or dioxane solution of the residue afforded by evaporation of the solvent in vacuo after the electrolysis. Cyclic secondary alcohols such as 3β-hydroxy steroids and 2-adamantanol are transformed into the corresponding fluorides in satisfactory yields when the geometry of the leaving group in 2 is suitable for the substitution or an elimination process for 2 to give an alkene is stereochemically forbidden. The fluorination of steroidal alcohols and 4-phenyl-1-cyclohexanol proceeded with complete inversion, demonstrating that a fluorine atom from the tetrafluoroborate anion attacks from the side opposite to the phosphonium moiety in 2 via an SN2 mechanism rather than an SN1 mechanism. The fluorination of acyclic secondary and primary alcohols was performed by the present method in reasonable yields, although the reaction for the latter required more forcing conditions, such as refluxing in dioxane.

Facile Preparation of Tetrabutylphosphonium Fluoride and Its HF Adducts. New Fluoride Anion Sources for Selective Nucleophilic Fluorination

Anhydrous tetrabutylphosphonium hydrogen bifluoride (2), dihydrogen trifluoride prepared from aq. tetrabutylphosphonium hydroxide and aq.HF, and tetrabutylphosphonium fluoride prepared from 2 and BunLi were shown to be useful fluoride sources for selective nucleophilic fluorination of oxiranes, alkyl halides, alcohols and sulfonates of aliphatic and steroidal species.

CHEMOSELECTIVE FLUORINATION FOR PRIMARY ALCOHOLS

Primary alcohols and their silylated derivatives are selectively fluorinated by tetraalkylammonium fluoride and aryl (or alkyl) sulfonyl fluoride.

Fluorination of carbanions with N-fluoro-N-alkylsulfonamides

Process for fluorinating an organic carbanion, which process comprises contacting and reacting, in a dry inert atmosphere, the compound of the formula selected from STR1 wherein STR2 is the carbanion, M is a counter ion, and X is a halide and a selected N-flouro-N-alkylsulfonamide.