
TY  - JOUR
A1  - Della, EW 
A1  - Tsanaktsidis, J 
T1  - Synthesis of Bridgehead Halides by Barton Halodecarboxylation
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 989
VL  - 42
IS  - 1
SP  - 61
EP  - 69
KW  - 
UR  - https://doi.org/10.1071/CH9890061 
N2  - Bridgehead carboxylic acids can be converted into their corresponding chlorides very efficiently under Barton halodecarboxylation conditions. Addition of the acid chloride to a suspension of the sodium salt of 1-hydroxypyridine-2(1H)- thione in boiling carbon tetrachloride under irradiation leads to excellent yields of the bridgehead chloride via the derived thiohydroxamic ester. In a useful modification for the synthesis of volatile halides, either 1,1,1-trichloro-2,2,2-trifluoroethane or trichlorofluoromethane can be employed as substitute solvents. It is found that the Barton procedure is applicable to the synthesis of labile bromides such as 1-bromobicyclo[3.1.1]heptane for which the usual Hunsdiecker reaction fails. For these, and other brominations , 2-bromo-2-chloro-1,1,1-trifluoroethane ('Halothane') is shown to function as an efficient solvent/bromine atom donor. 
ER  -

