e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Electron transfer process. 49. Radical and ionic reactions of (benzoylmethyl) mercurials

GA Russell, SV Kulkarni…

Index: Russell, Glen A.; Kulkarni, Shekhar V.; Khanna, Rajive K. Journal of Organic Chemistry, 1990 , vol. 55, # 3 p. 1080 - 1086

Full Text: HTML

Citation Number: 23

Abstract

Photolysis of PhCOCHzHgCl or (PhCOCH,) 2Hg yields benzoylmethyl radicals which can be trapped by anions such as Me2C= N02-, RC (C02Et),-, RC (O-)= CH2 or by other electron- rich systems such as (RO) 3P, N-methylpyrrole, enamines, or norbornene. Electron transfer from the adduct radicals to the mercurial yields PhCOCHzA from the anions A-, PhCOCH, P (O)(OR), from P (OR) 3, and the phenacyl derivative from N-methylpyrrole or enamines. ...

Diethyl malonate Structure

Diethyl malonate

~%

diethyl 2-phenacylpropanedioate Structure

diethyl 2-phena...

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

N/A Structure

~27%

diethyl 2-phenacylpropanedioate Structure

diethyl 2-phena...

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

Trimethyl phosphite Structure

Trimethyl phosphite

~%

Trimethyl phosphate Structure

Trimethyl phosphate

1,2,3,4-Tetraphenyl-1,4-butanedione Structure

1,2,3,4-Tetraph...

Detail

1-(trimethylsilyloxy)-cyclohex-1-ene Structure

1-(trimethylsil...

~12%

2-(2-OXO-2-PHENYL-ETHYL)-CYCLOHEXANONE Structure

2-(2-OXO-2-PHEN...

2-dimethoxyphosphoryl-1-phenylethanone Structure

2-dimethoxyphos...

Acetophenone Structure

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

Trimethyl phosphite Structure

Trimethyl phosphite

~%

Trimethyl phosphate Structure

Trimethyl phosphate

1,2,3,4-Tetraphenyl-1,4-butanedione Structure

1,2,3,4-Tetraph...

Detail

1-(trimethylsilyloxy)-cyclohex-1-ene Structure

1-(trimethylsil...

~%

2-(2-OXO-2-PHENYL-ETHYL)-CYCLOHEXANONE Structure

2-(2-OXO-2-PHEN...

2-dimethoxyphosphoryl-1-phenylethanone Structure

2-dimethoxyphos...

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

Trimethyl phosphite Structure

Trimethyl phosphite

~%

1,2,3,4-Tetraphenyl-1,4-butanedione Structure

1,2,3,4-Tetraph...

Chloromethane Structure

Detail

Phenyl ethyl ketone Structure

Phenyl ethyl ketone

~%

2-methyl-1,4-diphenylbutane-1,4-dione Structure

2-methyl-1,4-di...

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

N/A Structure

~24%

2-methyl-1,4-diphenylbutane-1,4-dione Structure

2-methyl-1,4-di...

nitromethane Structure

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

~3%

3-nitro-1-phenylpropan-1-one Structure

3-nitro-1-pheny...

(nitromethyl)mercury(II) chloride Structure

(nitromethyl)me...

Detail

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

diethyl methylmalonate anion Structure

diethyl methylm...

~59%

diethyl 2-methyl-2-phenacylpropanedioate Structure

diethyl 2-methy...

Ethyl methylmalonate Structure

Ethyl methylmalonate

~%

diethyl 2-methyl-2-phenacylpropanedioate Structure

diethyl 2-methy...

Pinacolone Structure

~%

5,5-DIMETHYL-1-PHENYL-HEXANE-1,4-DIONE Structure

5,5-DIMETHYL-1-...

pinacolone enolate anion Structure

pinacolone enol...

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

~37%

5,5-DIMETHYL-1-PHENYL-HEXANE-1,4-DIONE Structure

5,5-DIMETHYL-1-...

ethylnitronate(1-) Structure

ethylnitronate(1-)

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

~32%

N/A Structure

3-nitro-1-phenyl-butan-1-one Structure

3-nitro-1-pheny...

propane-2-nitronate Structure

propane-2-nitronate

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

~66%

Seneciophenone Structure

3-methyl-3-nitro-1-phenylbutan-1-one Structure

3-methyl-3-nitr...

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

Trimethyl phosphite Structure

Trimethyl phosphite

~13%

dimethyl 1-phenylethenyl phosphate Structure

dimethyl 1-phen...

N/A Structure

Detail

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

Trimethyl phosphite Structure

Trimethyl phosphite

~67%

dimethyl 1-phenylethenyl phosphate Structure

dimethyl 1-phen...

Acetophenone Structure

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

~%

2-(2-OXO-2-PHENYL-ETHYL)-CYCLOHEXANONE Structure

2-(2-OXO-2-PHEN...

1-(trimethylsilyloxy)-cyclohex-1-ene Structure

1-(trimethylsil...

~12%

2-(2-OXO-2-PHENYL-ETHYL)-CYCLOHEXANONE Structure

2-(2-OXO-2-PHEN...

2-dimethoxyphosphoryl-1-phenylethanone Structure

2-dimethoxyphos...

Acetophenone Structure

1-(trimethylsilyloxy)-cyclohex-1-ene Structure

1-(trimethylsil...

~%

2-(2-OXO-2-PHENYL-ETHYL)-CYCLOHEXANONE Structure

2-(2-OXO-2-PHEN...

2-dimethoxyphosphoryl-1-phenylethanone Structure

2-dimethoxyphos...

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

Triethyl phosphite Structure

Triethyl phosphite

~33%

1,2,3,4-Tetraphenyl-1,4-butanedione Structure

1,2,3,4-Tetraph...

DIETHYL (2-OXO-2-PHENYLETHYL)PHOSPHONATE Structure

DIETHYL (2-OXO-...

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

diphenylacetonitrile anion Structure

diphenylacetoni...

~70%

Butanedinitrile, 2,2,3,3-tetraphenyl- Structure

Butanedinitrile...

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

N/A Structure

~10%

Benzene,1,1'-(1-nitro-1,2-ethenediyl)bis- Structure

Benzene,1,1'-(1...

(1,2-dinitro-2-phenyl-ethyl)benzene Structure

(1,2-dinitro-2-...

Detail

deoxybenzoin enolate Structure

deoxybenzoin enolate

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

~4%

1,2,3,4-Tetraphenyl-1,4-butanedione Structure

1,2,3,4-Tetraph...

1,2,4-triphenylbutane-1,4-dione Structure

1,2,4-triphenyl...

(2-oxo-2-phenylethyl)mercury chloride Structure

(2-oxo-2-phenyl...

~4%

1,2,3,4-Tetraphenyl-1,4-butanedione Structure

1,2,3,4-Tetraph...

1,2,4-triphenylbutane-1,4-dione Structure

1,2,4-triphenyl...

2-Phenylacetophenone Structure

2-Phenylacetophenone

~%

1,2,4-triphenylbutane-1,4-dione Structure

1,2,4-triphenyl...

Carbon–carbon bond formation by radical addition–fragmentati...

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Radical Alkylations of Alkyl Halides and Unactivated CH Bond...

[Lee, Jin Young; Lim, Kyoung-Chan; Meng, Xiangjian; Kim, Sunggak Synlett, 2010 , # 11 p. 1647 - 1650]

Carbon–carbon bond formation by radical addition–fragmentati...

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Reaction of aryl chromium carbene complexes with ethyl propi...

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