RADICAL IONS AND PHOTOCHEMICAL CHARGE TRANSFER PHENOMENA. 36. PHOTOREACTIONS OF ENONES WITH AMINES - CYCLIZATION OF UNSATURATED ENONES AND REDUCTIVE RING-OPENING BY PHOTOINDUCED ELECTRON-TRANSFER (PET)

Mattay J, BANNING A, BISCHOF EW, HEIDBREDER A, RUNSINK J (1992)
Chemische Berichte 125(9): 2119-2127.

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Abstract
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 ring-enlarged 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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Mattay J, BANNING A, BISCHOF EW, HEIDBREDER A, RUNSINK J. RADICAL IONS AND PHOTOCHEMICAL CHARGE TRANSFER PHENOMENA. 36. PHOTOREACTIONS OF ENONES WITH AMINES - CYCLIZATION OF UNSATURATED ENONES AND REDUCTIVE RING-OPENING BY PHOTOINDUCED ELECTRON-TRANSFER (PET). Chemische Berichte. 1992;125(9):2119-2127.
Mattay, J., BANNING, A., BISCHOF, E. W., HEIDBREDER, A., & RUNSINK, J. (1992). RADICAL IONS AND PHOTOCHEMICAL CHARGE TRANSFER PHENOMENA. 36. PHOTOREACTIONS OF ENONES WITH AMINES - CYCLIZATION OF UNSATURATED ENONES AND REDUCTIVE RING-OPENING BY PHOTOINDUCED ELECTRON-TRANSFER (PET). Chemische Berichte, 125(9), 2119-2127.
Mattay, J., BANNING, A., BISCHOF, E. W., HEIDBREDER, A., and RUNSINK, J. (1992). RADICAL IONS AND PHOTOCHEMICAL CHARGE TRANSFER PHENOMENA. 36. PHOTOREACTIONS OF ENONES WITH AMINES - CYCLIZATION OF UNSATURATED ENONES AND REDUCTIVE RING-OPENING BY PHOTOINDUCED ELECTRON-TRANSFER (PET). Chemische Berichte 125, 2119-2127.
Mattay, J., et al., 1992. RADICAL IONS AND PHOTOCHEMICAL CHARGE TRANSFER PHENOMENA. 36. PHOTOREACTIONS OF ENONES WITH AMINES - CYCLIZATION OF UNSATURATED ENONES AND REDUCTIVE RING-OPENING BY PHOTOINDUCED ELECTRON-TRANSFER (PET). Chemische Berichte, 125(9), p 2119-2127.
J. Mattay, et al., “RADICAL IONS AND PHOTOCHEMICAL CHARGE TRANSFER PHENOMENA. 36. PHOTOREACTIONS OF ENONES WITH AMINES - CYCLIZATION OF UNSATURATED ENONES AND REDUCTIVE RING-OPENING BY PHOTOINDUCED ELECTRON-TRANSFER (PET)”, Chemische Berichte, vol. 125, 1992, pp. 2119-2127.
Mattay, J., BANNING, A., BISCHOF, E.W., HEIDBREDER, A., RUNSINK, J.: RADICAL IONS AND PHOTOCHEMICAL CHARGE TRANSFER PHENOMENA. 36. PHOTOREACTIONS OF ENONES WITH AMINES - CYCLIZATION OF UNSATURATED ENONES AND REDUCTIVE RING-OPENING BY PHOTOINDUCED ELECTRON-TRANSFER (PET). Chemische Berichte. 125, 2119-2127 (1992).
Mattay, Jochen, BANNING, A, BISCHOF, EW, HEIDBREDER, A, and RUNSINK, J. “RADICAL IONS AND PHOTOCHEMICAL CHARGE TRANSFER PHENOMENA. 36. PHOTOREACTIONS OF ENONES WITH AMINES - CYCLIZATION OF UNSATURATED ENONES AND REDUCTIVE RING-OPENING BY PHOTOINDUCED ELECTRON-TRANSFER (PET)”. Chemische Berichte 125.9 (1992): 2119-2127.
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