Protecting group release through photoinduced electron transfer: Wavelength control through sensitized irradiation

被引：35

作者：

Banerjee, A ^{[1
]}

Lee, K ^{[1
]}

Yu, Q ^{[1
]}

Fang, AG ^{[1
]}

Falvey, DE ^{[1
]}

机构：

[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 26期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(98)00857-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phenacyl esters (benzoylmethyl esters, PhCOCH2-OCOR) release carboxylic acids upon photolysis using photosensitizers that are good one-electron donors in the excited stale. Herein it is demonstrated that this procedure can be used to control the wavelength of light required to trigger the release. A variety of sensitizers having different absorption profiles are employed and in each case high isolated yields of carboxylic acids are achieved. it is further demonstrated that this method be extended into the visible (>400 nm) region of the Spectrum. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4635 / 4638

页数：4

共 9 条

[1]

[Anonymous], ORG PHOTOCHEM

[2] Protecting groups that can be removed through photochemical electron transfer: Mechanistic and product studies on photosensitized release of carboxylates from phenacyl esters [J].

Banerjee, A ;

Falvey, DE .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) :6245-6251

[3]

CORRIE JET, 1993, BIOL APPL PHOTOCHEMI, P243

[4] ELECTRON-TRANSFER PHOTOINDUCED FROM NAPHTHOLATE ANIONS - ANION OXIDATION POTENTIALS AND USE OF MARCUS FREE-ENERGY RELATIONSHIPS [J].

LEGROS, B ;

VANDEREECKEN, P ;

SOUMILLION, JP .

JOURNAL OF PHYSICAL CHEMISTRY, 1991, 95 (12) :4752-4761

[5] New photoactivated protecting groups .6. p-hydroxyphenacyl: A phototrigger for chemical and biochemical probes [J].

Park, CH ;

Givens, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (10) :2453-2463

[6] DIMETHOXYBENZOIN CARBONATES - PHOTOCHEMICALLY-REMOVABLE ALCOHOL PROTECTING GROUPS SUITABLE FOR PHOSPHORAMIDITE-BASED DNA-SYNTHESIS [J].

PIRRUNG, MC ;

BRADLEY, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1116-1117

[7] Model studies of DNA photorepair: Reduction potentials of thymine and cytosine cyclobutane dimers measured by fluorescence quenching [J].

Scannell, MP ;

Fenick, DJ ;

Yeh, SR ;

Falvey, DE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (08) :1971-1977

[8] FRAGMENTATION OF SUBSTITUTED ACETOPHENONE AND HALOBENZOPHENONE KETYLS - CALIBRATION OF A MECHANISTIC PROBE [J].

TANNER, DD ;

CHEN, JJ ;

CHEN, L ;

LUELO, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8074-8081

[9]

Willner I., 1993, BIOL APPL PHOTOCHEMI, P1

← 1 →