Photoreactions of Enones with Amines – Cyclization of Unsaturated Enones and Reductive Ring Opening by Photoinduced Electron Transfer (PET) | Zendy

Mattay Jochen | Zendy; Banning Anja | Zendy; Bischof Eric W. | Zendy; Heidbreder Andreas | Zendy; Runsink Jan | Zendy

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Photoreactions of Enones with Amines – Cyclization of Unsaturated Enones and Reductive Ring Opening by Photoinduced Electron Transfer (PET)

Author(s) -

Mattay Jochen,

Banning Anja,

Bischof Eric W.,

Heidbreder Andreas,

Runsink Jan

Publication year - 1992

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19921250921

Subject(s) - chemistry , cyclobutane , cycloaddition , regioselectivity , cyclopropane , ring (chemistry) , photoinduced electron transfer , electron transfer , photochemistry , cyclobutanes , photodissociation , medicinal chemistry , organic chemistry , catalysis

Photolysis of the unsaturated enones 1 yields [2 + 2] cycloaddition products 2 and 3 with varying regioselectivity. Under electron‐transfer conditions (PET) spirocyclic products 4 are formed. The straight [2 + 2] cycloaddition products 2b,c,f are converted to the spirocyclic products 4b,c,f under the same reaction conditions. The cyclobutane 5 and the cyclopropane 11 also undergo this new reductive ring opening reaction, while the stabilized system 7 is converted to reduced ringenlarged triquinane 10 which may be interesting in natural product synthesis. – Irradiation of 2‐cyclohexen‐1‐one ( 14 ) in the presence of N,N ‐dimethylallylamine ( 15 ) leads to the decahydroisoquinoline 18 . A mechanism involving radical intermediates is discussed.

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