Evidence for singlet state β cleavage in the photoreaction of α-(2,6-dimethoxyphenoxy)-acetophenone inferred from time-resolved CIDNP spectroscopy

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Evidence for singlet state β cleavage in the photoreaction of α-(2,6-dimethoxyphenoxy)-acetophenone inferred from time-resolved CIDNP spectroscopy. / Palm, W. U.; Dreeskamp, Herbert.
In: Journal of Photochemistry and Photobiology, A: Chemistry, Vol. 52, No. 3, 01.06.1990, p. 439-450.

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@article{13d0872fa14c4df7b999ed1fe7ec07e9,
title = "Evidence for singlet state β cleavage in the photoreaction of α-(2,6-dimethoxyphenoxy)-acetophenone inferred from time-resolved CIDNP spectroscopy",
abstract = "The photochemistry of α-(2,6-dimethoxyphenoxy)-acetophenone (1) was studied using CIDNP spectroscopy; an XeCl excimer laser (308 nm) and a 250 MHz 1H nuclear magnetic resonance (NMR) spectrometer were employed. The results are compared with the photoreactions of α-hydroxyacetophenone (2) and α-methoxyacetophenone (3). The CIDNP spectra of 1 can be interpreted as a result of a β cleavage from the singlet state. With time-resolved CIDNP spectroscopy it is possible to detect the enol of acetophenone in a second reaction path and to observe the tautomerization to acetophenone. Evidence is presented that this reaction path starts with the photoreduction of 1 from the triplet state. Compound 2 shows α cleavage from the triplet state and no β cleavage. As expected no CIDNP spectra are observed from 3 which is known to react via a Norrish type II mechanism.",
keywords = "Chemistry",
author = "Palm, {W. U.} and Herbert Dreeskamp",
year = "1990",
month = jun,
day = "1",
doi = "10.1016/1010-6030(90)85021-N",
language = "English",
volume = "52",
pages = "439--450",
journal = "Journal of Photochemistry and Photobiology, A: Chemistry",
issn = "1010-6030",
publisher = "Elsevier B.V.",
number = "3",

}

RIS

TY - JOUR

T1 - Evidence for singlet state β cleavage in the photoreaction of α-(2,6-dimethoxyphenoxy)-acetophenone inferred from time-resolved CIDNP spectroscopy

AU - Palm, W. U.

AU - Dreeskamp, Herbert

PY - 1990/6/1

Y1 - 1990/6/1

N2 - The photochemistry of α-(2,6-dimethoxyphenoxy)-acetophenone (1) was studied using CIDNP spectroscopy; an XeCl excimer laser (308 nm) and a 250 MHz 1H nuclear magnetic resonance (NMR) spectrometer were employed. The results are compared with the photoreactions of α-hydroxyacetophenone (2) and α-methoxyacetophenone (3). The CIDNP spectra of 1 can be interpreted as a result of a β cleavage from the singlet state. With time-resolved CIDNP spectroscopy it is possible to detect the enol of acetophenone in a second reaction path and to observe the tautomerization to acetophenone. Evidence is presented that this reaction path starts with the photoreduction of 1 from the triplet state. Compound 2 shows α cleavage from the triplet state and no β cleavage. As expected no CIDNP spectra are observed from 3 which is known to react via a Norrish type II mechanism.

AB - The photochemistry of α-(2,6-dimethoxyphenoxy)-acetophenone (1) was studied using CIDNP spectroscopy; an XeCl excimer laser (308 nm) and a 250 MHz 1H nuclear magnetic resonance (NMR) spectrometer were employed. The results are compared with the photoreactions of α-hydroxyacetophenone (2) and α-methoxyacetophenone (3). The CIDNP spectra of 1 can be interpreted as a result of a β cleavage from the singlet state. With time-resolved CIDNP spectroscopy it is possible to detect the enol of acetophenone in a second reaction path and to observe the tautomerization to acetophenone. Evidence is presented that this reaction path starts with the photoreduction of 1 from the triplet state. Compound 2 shows α cleavage from the triplet state and no β cleavage. As expected no CIDNP spectra are observed from 3 which is known to react via a Norrish type II mechanism.

KW - Chemistry

UR - http://www.scopus.com/inward/record.url?scp=0000049828&partnerID=8YFLogxK

U2 - 10.1016/1010-6030(90)85021-N

DO - 10.1016/1010-6030(90)85021-N

M3 - Journal articles

AN - SCOPUS:0000049828

VL - 52

SP - 439

EP - 450

JO - Journal of Photochemistry and Photobiology, A: Chemistry

JF - Journal of Photochemistry and Photobiology, A: Chemistry

SN - 1010-6030

IS - 3

ER -