- 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
- Wempe, Michael F.,Grunwell, John R.
-
-
Read Online
- 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.
- Wu, Fu-Peng,Li, Da,Peng, Jin-Bao,Wu, Xiao-Feng
-
supporting information
p. 5699 - 5703
(2019/08/01)
-
- 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
- Gauthier, Donald R.,Rivera, Nelo R.,Yang, Haifeng,Schultz, Danielle M.,Shultz, C. Scott
-
supporting information
p. 15596 - 15600
(2018/11/23)
-
- 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
- -
-
Page/Page column 17-18
(2010/03/05)
-
- 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
- -
-
Page/Page column 25-26; 28
(2008/06/13)
-
- 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
- -
-
Page/Page column 27
(2008/06/13)
-
- 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.
- Itsenko, Oleksiy,Langstroem, Bengt
-
p. 2244 - 2249
(2007/10/03)
-
- 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.
- Grunwell,Wempe,Mitchell,Grunwell
-
p. 7163 - 7166
(2007/10/02)
-