- 2-Hydroxy-1,2,2-triphenylethanone as an efficient photolabile protecting group for carboxylic acids
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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.
- Ashraf, M. Arfan,Russell, Alexander G.,Wharton, Christopher W.,Snaith, John S.
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p. 586 - 593
(2007/10/03)
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- Synthesis and photolysis studies of carboxylic esters of 2-hydroxy-1,2,2-triphenylethanone: A novel tandem photocyclisation
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Carboxylic esters of 2-hydroxy-1,2,2-triphenylethanone can be prepared in good yield by reaction between 2-chloro-1,2,2-triphenylethanone and a carboxylic acid in the presence of silver carbonate and silver tetrafluoroborate. Irradiation of the ester with a medium pressure mercury lamp results in a rapid and quantitative photolysis to afford the carboxylic acid and benzo[b]phenanthro[9,10-d]furan.
- Ashraf, M. Arfan,Jones, Matthew A.,Kelly, Natalie E.,Mullaney, Alex,Snaith, John S.,Williams, Iwan
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p. 3151 - 3154
(2007/10/03)
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