Norrish Type II Processes of Ketones: Influence of Environment

Hasegawa, Tadashi

doi:10.1002/chin.200416275

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2011

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“…One important chemical pathway for the deactivation of ketones from the electronically excited states is photoinduced H-abstraction [ 7 ]. Intermolecular photoinduced H-abstraction leads principally to the reduction of the ketone [ 8 – 12 ], whereas intramolecular H-abstraction [ 13 – 14 ] leads to cyclization [ 15 – 17 ] or fragmentation, the so called Norish type II reaction [ 18 – 20 ]. The photochemistry of phthalimide derivatives is often similar to that of simple ketones [ 21 – 33 ].…”

Section: Introductionmentioning

confidence: 99%

Photoinduced homolytic C–H activation inN-(4-homoadamantyl)phthalimide

Cindro¹,

Horvat²,

Mlinarić‐Majerski³

et al. 2011

Beilstein J. Org. Chem.

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Summary N-(4-homoadamantyl)phthalimide (5) on excitation and population of the triplet excited state underwent intramolecular H-abstractions and gave products 6 and 7. The major product, exo-alcohol 6 was a result of the regioselective δ H-abstraction and the stereoselective cyclization of the 1,5-biradical. Minor products 7 were formed by photoinduced γ H-abstractions, followed by ring closure to azetidinols and ring enlargement to azepinediones. The observed selectivity to exo-alcohol 6 was explained by the conformation of 5 and the best orientation and the availability of the δ-H for the abstraction.

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