Temperature dependent product distribution in photolysis of o-alkylphenacyl benzoates

Mi Jang; Bum Hee Lim; Hyuk Jun Ryu; Bong Ser Park

doi:10.1016/j.tetlet.2013.10.109

Temperature dependent product distribution in photolysis of o-alkylphenacyl benzoates

Mi Jang, Bum Hee Lim, Hyuk Jun Ryu, Bong Ser Park

Department of Chemistry

Dongguk University

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

Temperature effect on photochemical reactions of ortho-alkylphenacyl benzoates, one of the recently developed photoremovable protecting groups (PPG), giving indanones (IN) and benzocyclobutenols (CB) was examined. As temperature was lowered, CB was formed preferentially over IN and the amount of IN increased as temperature was elevated. Arrhenius plot of ln(IN/CB) versus 1/T gave a straight line from which Ea_IN-Ea_CB and A _IN/A_CB were obtained. The least sterically hindered 2-methylphenacyl benzoate (1) gave the highest Ea_IN-Ea_CB and A_IN/A_CB among the ortho-alkylphenacyl benzoates tested in this research including 2,4,6-trimethylphenacyl benzoate (2) and 2,4,6-triisopropylphenacyl benzoate (3).

Original language	English
Pages (from-to)	7175-7179
Number of pages	5
Journal	Tetrahedron Letters
Volume	54
Issue number	52
DOIs	https://doi.org/10.1016/j.tetlet.2013.10.109
State	Published - 25 Dec 2013

Keywords

Benzocyclobutenol
Photochemistry
Photoremovable protecting group
Temperature effect

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10.1016/j.tetlet.2013.10.109

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title = "Temperature dependent product distribution in photolysis of o-alkylphenacyl benzoates",

abstract = "Temperature effect on photochemical reactions of ortho-alkylphenacyl benzoates, one of the recently developed photoremovable protecting groups (PPG), giving indanones (IN) and benzocyclobutenols (CB) was examined. As temperature was lowered, CB was formed preferentially over IN and the amount of IN increased as temperature was elevated. Arrhenius plot of ln(IN/CB) versus 1/T gave a straight line from which EaIN-EaCB and A IN/ACB were obtained. The least sterically hindered 2-methylphenacyl benzoate (1) gave the highest EaIN-EaCB and AIN/ACB among the ortho-alkylphenacyl benzoates tested in this research including 2,4,6-trimethylphenacyl benzoate (2) and 2,4,6-triisopropylphenacyl benzoate (3).",

keywords = "Benzocyclobutenol, Photochemistry, Photoremovable protecting group, Temperature effect",

author = "Mi Jang and Lim, {Bum Hee} and Ryu, {Hyuk Jun} and Park, {Bong Ser}",

year = "2013",

month = dec,

day = "25",

doi = "10.1016/j.tetlet.2013.10.109",

language = "English",

volume = "54",

pages = "7175--7179",

journal = "Tetrahedron Letters",

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number = "52",

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TY - JOUR

T1 - Temperature dependent product distribution in photolysis of o-alkylphenacyl benzoates

AU - Jang, Mi

AU - Lim, Bum Hee

AU - Ryu, Hyuk Jun

AU - Park, Bong Ser

PY - 2013/12/25

Y1 - 2013/12/25

N2 - Temperature effect on photochemical reactions of ortho-alkylphenacyl benzoates, one of the recently developed photoremovable protecting groups (PPG), giving indanones (IN) and benzocyclobutenols (CB) was examined. As temperature was lowered, CB was formed preferentially over IN and the amount of IN increased as temperature was elevated. Arrhenius plot of ln(IN/CB) versus 1/T gave a straight line from which EaIN-EaCB and A IN/ACB were obtained. The least sterically hindered 2-methylphenacyl benzoate (1) gave the highest EaIN-EaCB and AIN/ACB among the ortho-alkylphenacyl benzoates tested in this research including 2,4,6-trimethylphenacyl benzoate (2) and 2,4,6-triisopropylphenacyl benzoate (3).

AB - Temperature effect on photochemical reactions of ortho-alkylphenacyl benzoates, one of the recently developed photoremovable protecting groups (PPG), giving indanones (IN) and benzocyclobutenols (CB) was examined. As temperature was lowered, CB was formed preferentially over IN and the amount of IN increased as temperature was elevated. Arrhenius plot of ln(IN/CB) versus 1/T gave a straight line from which EaIN-EaCB and A IN/ACB were obtained. The least sterically hindered 2-methylphenacyl benzoate (1) gave the highest EaIN-EaCB and AIN/ACB among the ortho-alkylphenacyl benzoates tested in this research including 2,4,6-trimethylphenacyl benzoate (2) and 2,4,6-triisopropylphenacyl benzoate (3).

KW - Benzocyclobutenol

KW - Photochemistry

KW - Photoremovable protecting group

KW - Temperature effect

UR - http://www.scopus.com/inward/record.url?scp=84888135256&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2013.10.109

DO - 10.1016/j.tetlet.2013.10.109

M3 - Article

AN - SCOPUS:84888135256

SN - 0040-4039

VL - 54

SP - 7175

EP - 7179

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 52

ER -

Temperature dependent product distribution in photolysis of o-alkylphenacyl benzoates

Abstract

Keywords

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