TY - JOUR
T1 - 2-Hydroxy-1,2,2-triphenylethanone as an efficient photolabile protecting group for carboxylic acids
AU - Ashraf, MA
AU - Russell, Alexander
AU - Wharton, Christopher
AU - Snaith, John
PY - 2007/1/15
Y1 - 2007/1/15
N2 - The synthesis is reported of 2-hydroxy- 1,2,2-triphenylethanone esters of carboxylic acids by the reaction between 2-chloro-1,2,2-triphenylethanone and a carboxylic acid in the presence of silver carbonate and silver tetrafluoroborate. Photolysis of the esters occurs rapidly on irradiation with a medium-pressure mercury lamp through quartz or Pyrex to return the carboxylic acid. The side product of the photolysis is benzo[b]phenanthro[9, 10-d]furan, formed through a tandem process involving initial generation of 2,3-diphenylbenzofuran, photochemical cyclisation and re-aromatisation by aerial oxidation. (c) 2006 Elsevier Ltd. All rights reserved.
AB - The synthesis is reported of 2-hydroxy- 1,2,2-triphenylethanone esters of carboxylic acids by the reaction between 2-chloro-1,2,2-triphenylethanone and a carboxylic acid in the presence of silver carbonate and silver tetrafluoroborate. Photolysis of the esters occurs rapidly on irradiation with a medium-pressure mercury lamp through quartz or Pyrex to return the carboxylic acid. The side product of the photolysis is benzo[b]phenanthro[9, 10-d]furan, formed through a tandem process involving initial generation of 2,3-diphenylbenzofuran, photochemical cyclisation and re-aromatisation by aerial oxidation. (c) 2006 Elsevier Ltd. All rights reserved.
U2 - 10.1016/j.tet.2006.11.015
DO - 10.1016/j.tet.2006.11.015
M3 - Article
VL - 63
SP - 586
EP - 593
JO - Tetrahedron
JF - Tetrahedron
IS - 3
ER -