Rearrangement of 2-Quinolyl- and 1-Isoquinolylcarbenes to Naphthylnitrenes

• Published in: Journal of organic chemistry Vol. 69; no. 6; pp. 2033 - 2036
• Main Authors: Lân, Nguyen Mong, Burgard, Riko, Wentrup, Curt
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 19.03.2004; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; AZIRINES; SPECTROSCOPY; RING CONTRACTION; NITRENES; CARBENES; AB-INITIO; Chemical rearrangement; Under vacuum; Tetrazole derivatives; Isoquinoline derivatives; Nitrile; Organic azide; Nitrogen heterocycle; Isomerization; Quinoline derivatives; Nitrene; Flash pyrolysis; Imine; Naphthalene derivatives; Ketenes; Ring cleavage; Hydrogen abstraction; Carbene; Chemical activation; Photolysis; Triazole derivatives; Ring contraction; Dimer; Indene derivatives

2-Quinolylcarbene 23 and 1-isoquinolylcarbene 33 are generated by flash vacuum thermolysis (FVT) of the corresponding triazolo[1,5-a]quinoline and triazolo[5,1-a]isoquinoline 19 and 29, as well as 2-(5-tetrazolyl)quinoline and 1-(5-tetrazolyl)isoquinoline 20 and 30, respectively. These carbenes rear...