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

• Baiba Turovska,
• Henning Lund,
• Viesturs Lūsis,
• Anna Lielpētere,
• Edvards Liepiņš,
• Sergejs Beljakovs,
• Inguna Goba and
• Jānis Stradiņš

Beilstein J. Org. Chem. 2015, 11, 2166–2170, doi:10.3762/bjoc.11.234

• , Langelandsgade 140, DK 8000 Aarhus, Denmark 10.3762/bjoc.11.234 Abstract 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. Keywords: heterocyclic hydroperoxide; oxaziridine

• asymmetric oxidations. We have found a sunlight activated reaction of 1,2,3,4-tetrahydropiridine with dioxygen (3O2) producing stable heterocyclic hydroperoxide in excellent yield. The reaction has significant advantages as it uses cost-free reagents: light and dioxygen. The same reaction demonstrated the