Radical ions and photochemical charge-transfer phenomena. 39. Cycloadditions. 42. Radical cation [3 + 2] cycloadditions of 2H-azirines. Mechanistic studies concerning the intermediate radical cation

1993 ◽  
Vol 58 (16) ◽  
pp. 4462-4464 ◽  
Author(s):  
Felix Mueller ◽  
Jochen Mattay ◽  
Steen Steenken
1984 ◽  
Vol 39 (6) ◽  
pp. 763-770 ◽  
Author(s):  
Hans Bock ◽  
Wolfgang Kaim ◽  
Mitsuo Kira ◽  
Louis Réné ◽  
Heinz-Günther Viehe

AbstractThe photoelectron (PE) spectra of bis(dialkylamino) acetylenes R2N-C≡C-NR2 and of tetrakis(dialkylamino) allenes (R2N)2C=C=C(NR2)2 with R = CH3, C2H5 exhibit characteristic ionization patterns which are assigned to π radical cation states of the two molecular halves twisted against each other. The low first ionization potentials between 7.0 eV and 7.7 eV stimu­lated attempts to oxidize using AlCl3 in H2CCl2 or D2CCl2. The hyperfine structured ESR spectra observed can be unequivocally assigned to the ethylene radical cations R2N-HC=CH -NR2˙⊕ which are formed from the obviously non-persistent species R2N-C≡C-NR2˙⊕ via a hydrogen transfer. During the oxidation of the dialkylamino-substituted allenes no paramagnetic intermedi­ates could be detected, presumably due to a rapid dimerisation of the allene radical cation (R2N)2C=C=C(NR2)2˙⊕.


2000 ◽  
Vol 195-196 ◽  
pp. 85-99 ◽  
Author(s):  
Lorne M Fell ◽  
Paul J.A Ruttink ◽  
Peter C Burgers ◽  
Moschoula A Trikoupis ◽  
Johan K Terlouw

Tetrahedron ◽  
2000 ◽  
Vol 56 (25) ◽  
pp. 4117-4128 ◽  
Author(s):  
Ralf Glatthar ◽  
Martin Spichty ◽  
Andreas Gugger ◽  
Rohit Batra ◽  
Wolfgang Damm ◽  
...  

1972 ◽  
Vol 37 (10) ◽  
pp. 1485-1491 ◽  
Author(s):  
John W. Happ ◽  
John A. Ferguson ◽  
David G. Whitten
Keyword(s):  

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