59616-73-8

Upstream product

• 4119-41-9 1-iodo-3-phenylpropan 
• 1641-69-6 [13C]Carbon monoxide 
• 18496-54-3 phenylbutyric acid chloride 
• 300-57-2 allylbenzene 
• 166111-39-3 [1-13C]-4-Phenylbutyronitrile 

Relevant academic research and scientific papers

The Transannular Rearrangement of 5-Cyclodecynone

The acid-catalyzed rearrangement of 5-cyclodecynone (1) to bicyclo-1(6)-decen-2-one (5) has been investigated via 13C and deuterium labeling experiments, which showed that the transannular rearrangement proceeds by a mechanism not involving an enol

Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals

In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.

Palladium-Catalyzed Carbon Isotope Exchange on Aliphatic and Benzoic Acid Chlorides

An operationally simple protocol for a palladium-catalyzed 13CO and 14CO exchange with activated aliphatic and benzoic carbonyls is presented. Several 13C and 14C building blocks, natural product derivatives, an

Method for the use of [11C] carbon monoxide in labeling synthesis of 11C-labelled acids by photo-induced free radical carbonylation

Methods and reagents for photo-initiated carbonylation with carbon-isotope labeled carbon monoxide using alkyl/aryl iodides with water pretreated by a base are provided. The resultant carbon-isotope labeled acids are useful as radiopharmaceuticals, especi

METHOD FOR THE USE OF [11C] CARBON MONOXIDE IN LABELING SYNTHESIS OF 11C-LABELLED ACIDS BY PHOTO-INDUCED FREE RADICAL CARBONYLATION UNDER MILD CONDITIONS USING SULFOXIDES

Methods and reagents for photo-initiated carbonylation with carbon-isotope labeled carbon monoxide using alkyl/aryl iodides with sulfoxides and triethylamine are provided. The resultant carbon-isotope labeled acids, and pharmaceutical acceptable salts and

METHOD FOR THE USE OF [11C] CARBON MONOXIDE IN LABELING SYNTHESIS OF 11C-LABELLED ACIDS BY PHOTO-INDUCED FREE RADICAL CARBONYLATION

Methods and reagents for photo-initiated carbonylation with carbon-isotope labeled carbon monoxide using alkyl/aryl iodides with water pretreated by a base are provided. The resultant carbon-isotope labeled acids are useful as radiopharmaceuticals, especi

Radical-mediated carboxylation of alkyl iodides with [11C]carbon monoxide in solvent mixtures

(Chemical Equation Presented) [carboxyl-11C]Carboxylic acids were prepared from alkyl iodides via photoinitiated radical reactions using 10-8 mol of [11C]carbon monoxide in binary and ternary homogeneous solvent mixtures. Short-(isobutyric), medium-, and long-chain saturated fatty acids (heptadecanoic) were labeled with isolated decay-corrected radiochemical yields ranging from 55% to 70% in 5-7-min reactions. The conversion of [11C]carbon monoxide to products reached 80-90%. To obtain good yields in the reactions performed in water-acetonitrile and water-THF mixtures, the addition of tetrabutylammonium hydroxide or potassium hydroxide was essential. The carboxylation was efficient for primary and secondary alkyl iodides. The carboxylation of tertiary iodides was feasible for 1-iodoadamantane but not for tert-butyl iodide. The dependence of the radiochemical yields on reaction time, photoirradiation conditions, and organic and inorganic additives was studied. The method provides a one-step route to [carboxyl-11C]carboxylic acids; traditional methods, in contrast, would require several steps. For example, using the devised reaction conditions, 3.19 GBq of purified [1-11C]1,10-decanedicarboxylic acid (specific radioactivity 188 GBq/μmol) was obtained within 35 min of the end of 10 μAh bombardment. (1-13C)4-Phenylbutyric acid was synthesized using (13C)-carbon monoxide for identifying the labeling position with 1H and 13C NMR.

The transannular rearrangement of 5-cyclodecynone

The acid catalyzed rearrangement of 5-cyclodecynone to bicyclo[4.4.0]-1(6)-decen-2-one has been shown by carbon thirteen labeling experiments to proceed by a mechanism that does not involve an enol of 5-cyclodecynone.