2-Hydroxy-1,2,2-triphenylethanone as an efficient photolabile protecting group for carboxylic acids

MA Ashraf; Alexander Russell; Christopher Wharton; John Snaith

doi:10.1016/j.tet.2006.11.015

2-Hydroxy-1,2,2-triphenylethanone as an efficient photolabile protecting group for carboxylic acids

MA Ashraf
, Alexander Russell
, Christopher Wharton
, John Snaith

Research output: Contribution to journal › Article

16 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	586-593
Number of pages	8
Journal	Tetrahedron
Volume	63
Issue number	3
DOIs	https://doi.org/10.1016/j.tet.2006.11.015
Publication status	Published - 15 Jan 2007

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title = "2-Hydroxy-1,2,2-triphenylethanone as an efficient photolabile protecting group for carboxylic acids",

abstract = "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.",

author = "MA Ashraf and Alexander Russell and Christopher Wharton and John Snaith",

year = "2007",

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doi = "10.1016/j.tet.2006.11.015",

language = "English",

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pages = "586--593",

journal = "Tetrahedron",

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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 -

2-Hydroxy-1,2,2-triphenylethanone as an efficient photolabile protecting group for carboxylic acids

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