Photoinduced 1,2,3,4-tetrahydropyridine ring conversions

Stable heterocyclic hydroperoxide can be easily prepared as a product of fast oxidation of a 1,2,3,4-tetrahydropyridine by 3O2 if the solution is exposed to sunlight. The driving force for the photoinduced electron transfer is calculated from electrochemical and spectroscopic data. The outcome of th...

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Main Authors: Baiba Turovska, Henning Lund, Viesturs Lūsis, Anna Lielpētere, Edvards Liepiņš, Sergejs Beljakovs, Inguna Goba, Jānis Stradiņš
Format: Article
Language:English
Published: Beilstein-Institut 2015-11-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.11.234
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author Baiba Turovska
Henning Lund
Viesturs Lūsis
Anna Lielpētere
Edvards Liepiņš
Sergejs Beljakovs
Inguna Goba
Jānis Stradiņš
author_facet Baiba Turovska
Henning Lund
Viesturs Lūsis
Anna Lielpētere
Edvards Liepiņš
Sergejs Beljakovs
Inguna Goba
Jānis Stradiņš
author_sort Baiba Turovska
collection DOAJ
description Stable heterocyclic hydroperoxide can be easily prepared as a product of fast oxidation of a 1,2,3,4-tetrahydropyridine by 3O2 if the solution is exposed to sunlight. The driving force for the photoinduced electron transfer is calculated from electrochemical and spectroscopic data. The outcome of the reaction depends on the light intensity and the concentration of O2. In the solid state the heterocyclic hydroperoxide is stable; in solution it is involved in further reactions.
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spelling doaj.art-e98cbc4874fa4160bf56147a0e4559232022-12-21T22:11:52ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-11-011112166217010.3762/bjoc.11.2341860-5397-11-234Photoinduced 1,2,3,4-tetrahydropyridine ring conversionsBaiba Turovska0Henning Lund1Viesturs Lūsis2Anna Lielpētere3Edvards Liepiņš4Sergejs Beljakovs5Inguna Goba6Jānis Stradiņš7Physical-organic Chemistry Laboratory, Latvian Institute of Organic Synthesis, 21 Aizkraukles Str., Riga LV-1006, LatviaDepartment of Organic Chemistry, Aarhus University, Langelandsgade 140, DK 8000 Aarhus, DenmarkPhysical-organic Chemistry Laboratory, Latvian Institute of Organic Synthesis, 21 Aizkraukles Str., Riga LV-1006, LatviaPhysical-organic Chemistry Laboratory, Latvian Institute of Organic Synthesis, 21 Aizkraukles Str., Riga LV-1006, LatviaPhysical-organic Chemistry Laboratory, Latvian Institute of Organic Synthesis, 21 Aizkraukles Str., Riga LV-1006, LatviaPhysical-organic Chemistry Laboratory, Latvian Institute of Organic Synthesis, 21 Aizkraukles Str., Riga LV-1006, LatviaPhysical-organic Chemistry Laboratory, Latvian Institute of Organic Synthesis, 21 Aizkraukles Str., Riga LV-1006, LatviaPhysical-organic Chemistry Laboratory, Latvian Institute of Organic Synthesis, 21 Aizkraukles Str., Riga LV-1006, LatviaStable heterocyclic hydroperoxide can be easily prepared as a product of fast oxidation of a 1,2,3,4-tetrahydropyridine by 3O2 if the solution is exposed to sunlight. The driving force for the photoinduced electron transfer is calculated from electrochemical and spectroscopic data. The outcome of the reaction depends on the light intensity and the concentration of O2. In the solid state the heterocyclic hydroperoxide is stable; in solution it is involved in further reactions.https://doi.org/10.3762/bjoc.11.234heterocyclic hydroperoxideoxaziridinephotoinduced electron transferpyrrolidinetetrahydropyridine
spellingShingle Baiba Turovska
Henning Lund
Viesturs Lūsis
Anna Lielpētere
Edvards Liepiņš
Sergejs Beljakovs
Inguna Goba
Jānis Stradiņš
Photoinduced 1,2,3,4-tetrahydropyridine ring conversions
Beilstein Journal of Organic Chemistry
heterocyclic hydroperoxide
oxaziridine
photoinduced electron transfer
pyrrolidine
tetrahydropyridine
title Photoinduced 1,2,3,4-tetrahydropyridine ring conversions
title_full Photoinduced 1,2,3,4-tetrahydropyridine ring conversions
title_fullStr Photoinduced 1,2,3,4-tetrahydropyridine ring conversions
title_full_unstemmed Photoinduced 1,2,3,4-tetrahydropyridine ring conversions
title_short Photoinduced 1,2,3,4-tetrahydropyridine ring conversions
title_sort photoinduced 1 2 3 4 tetrahydropyridine ring conversions
topic heterocyclic hydroperoxide
oxaziridine
photoinduced electron transfer
pyrrolidine
tetrahydropyridine
url https://doi.org/10.3762/bjoc.11.234
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