Oxidative photofragmentation of .alpha.,.beta.-amino alcohols via single electron transfer: cooperative reactivity of donor and acceptor ion radicals in photogenerated contact radical ion pairs

The radical anion of dimesityltetraketone (ERed, I = -0.40 V) is easily generated in THF by potassium mirror/[2.2.2]-cryptand reduction. Its contact ion pairs with Na⊕, Cs⊕ and Ba⊕⊕ counter cations, prepared in THF solution by single electron transfer from the respective metals, are characterized by their ESR/ENDOR spectra, which exhibit temperature-dependent metal couplings of aNa⊕ = 0.061 mT (190 K), aCs⊕ = 0.021 mT (190 K), and aBa⊕⊕ = 0.145 mT (295 K).

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ChemInform Abstract: Photofragmentation via Single-Electron Transfer: Selective Labilization of C-C Bonds in Amino Alcohols with Several Bonds Between Heteroatom Substituents.

ChemInform ◽

10.1002/chin.198932098 ◽

1989 ◽

Vol 20 (32) ◽

Author(s):

X. CI ◽

D. G. WHITTEN

Keyword(s):

Electron Transfer ◽

Amino Alcohols ◽

Single Electron ◽

Single Electron Transfer

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Radical cyclization reactions of .alpha.-silyl amine .alpha.,.beta.-unsaturated ketone and ester systems promoted by single electron transfer photosensitization

Journal of the American Chemical Society ◽

10.1021/ja00023a038 ◽

1991 ◽

Vol 113 (23) ◽

pp. 8847-8863 ◽

Cited By ~ 70

Author(s):

Yoon T. Jeon ◽

Chao Pin Lee ◽

Patrick S. Mariano

Keyword(s):

Electron Transfer ◽

Radical Cyclization ◽

Single Electron ◽

Unsaturated Ketone ◽

Single Electron Transfer ◽

Cyclization Reactions ◽

Alpha Beta

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Exploratory study on photoinduced single electron transfer reactions of .alpha.,.beta.-epoxy ketones with amines

The Journal of Organic Chemistry ◽

10.1021/jo00004a052 ◽

1991 ◽

Vol 56 (4) ◽

pp. 1631-1635 ◽

Cited By ~ 60

Author(s):

Eietsu Hasegawa ◽

Kenyuki Ishiyama ◽

Takaaki Horaguchi ◽

Takahachi Shimizu

Keyword(s):

Electron Transfer ◽

Exploratory Study ◽

Single Electron ◽

Transfer Reactions ◽

Single Electron Transfer ◽

Electron Transfer Reactions ◽

Alpha Beta ◽

Epoxy Ketones

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Exploratory study on photoinduced single electron transfer reactions of .alpha.,.beta.-epoxy ketones with amines [Erratum to document cited in CA114(15):142987y]

The Journal of Organic Chemistry ◽

10.1021/jo00017a050 ◽

1991 ◽

Vol 56 (17) ◽

pp. 5236-5236 ◽

Cited By ~ 2

Author(s):

Eietsu Hasegawa ◽

Kenyuki Ishiyama ◽

Takaaki Horaguchi ◽

Takahachi Shimizu

Keyword(s):

Electron Transfer ◽

Exploratory Study ◽

Single Electron ◽

Transfer Reactions ◽

Single Electron Transfer ◽

Electron Transfer Reactions ◽

Alpha Beta ◽

Epoxy Ketones

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Photofragmentation via single-electron transfer: selective labilization of carbon-carbon bonds in amino alcohols with several bonds between heteroatom substituents

Journal of the American Chemical Society ◽

10.1021/ja00191a069 ◽

1989 ◽

Vol 111 (9) ◽

pp. 3459-3461 ◽

Cited By ~ 24

Author(s):

Xiaohong Ci ◽

David G. Whitten

Keyword(s):

Electron Transfer ◽

Amino Alcohols ◽

Single Electron ◽

Single Electron Transfer ◽

Carbon Carbon Bonds ◽

Carbon Bonds

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Reversal of Polarity by Catalytic SET Oxidation: Synthesis of Azabicyclo[m.n.o]alkanes via Chemoselective Reduction of Amidines

Organic & Biomolecular Chemistry ◽

10.1039/d1ob00416f ◽

2021 ◽

Author(s):

Sundarababu Baskaran ◽

Kirana D V ◽

Kanak Kanti Das

Keyword(s):

Electron Transfer ◽

Stereoselective Synthesis ◽

Single Electron ◽

Single Electron Transfer ◽

Catalytic Method ◽

One Pot ◽

Oxidative System ◽

Oxidation Synthesis

A one-pot catalytic method has been developed for the stereoselective synthesis of cyclopropane-fused cyclic amidines using CuBr2/K2S2O8 as an efficient single electron transfer (SET) oxidative system. The generality of this...

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