Mechanism of the reaction of carbon and nitrogen nucleophiles with the model carcinogens O-pivaloyl-N-arylhydroxylamines: competing SN2 substitution and SN1 solvolysis

1991 ◽  
Vol 113 (9) ◽  
pp. 3459-3466 ◽  
Author(s):  
John S. Helmick ◽  
Kristy A. Martin ◽  
Julie L. Heinrich ◽  
Michael Novak
Keyword(s):  
Carbon And Nitrogen ◽  
Nitrogen Nucleophiles ◽  
Mechanism Of The Reaction

Acyl cyanides as carbonyl heterodienophiles: application to the synthesis of naphthols, isoquinolones, and isocoumarins

1996 ◽  
Vol 74 (2) ◽  
pp. 221-226 ◽  
Author(s):  
Richard Connors ◽  
Elisabeth Tran ◽  
Tony Durst
Keyword(s):  
Key Words ◽  
Diels Alder ◽  
Acetonitrile Solution ◽  
Carbon And Nitrogen ◽  
Nitrogen Nucleophiles ◽  
Derivatives Of

Irradiation of 2-methylbenzoyl cyanide (3a) in acetonitrile solution results in the formation of its dimer, which upon loss of HCN gives rise to the cycloadduct 7a. The dimerization also proceeds efficiently with derivatives of 3a giving adducts 7b and 7c. When 2-methylaroyl cyanides are photolyzed in the presence of a more reactive acyl cyanide the mixed adducts 8a–e are obtained in excellent yields. The cycloadducts 7a–c and 8a–e react with carbon and nitrogen nucleophiles by a tandem addition–cyclization sequence furnishing substituted naphthols (10a and 10b) and isoquinolones (11a–d), respectively. Isocoumarins 12a and 12b were prepared from the adducts 8a and 8e by treatment with potassium tert-butoxide in THF. Key words: naphthols, isoquinolones, isocoumarins, synthesis of; acyl cyanides; hetero Diels–Alder.

scholarly journals Michael Addition of Carbon and Nitrogen Nucleophiles with Chalcone Catalyzed by Semicarbazide

2014 ◽  
Vol 34 (10) ◽  
pp. 2083
Author(s):  
Helong Cheng ◽  
Yuhua Gao ◽  
Shipeng Nie ◽  
Hongfei Lu
Keyword(s):  
Michael Addition ◽  
Carbon And Nitrogen ◽  
Nitrogen Nucleophiles
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