Stable carbonium ions. LXVII. Halonium ion formation via 1,4-halogen participation. Five-membered-ring tetramethylenehalonium, 2-methyltetramethylenehalonium, and 2,5-dimethyltetramethylenehalonium ions

1968 ◽  
Vol 90 (17) ◽  
pp. 4675-4678 ◽  
Author(s):  
George A. Olah ◽  
Paul E. Peterson
Keyword(s):  
Membered Ring ◽  
Ion Formation ◽  
Carbonium Ions ◽  
Halonium Ion

Stable carbonium ions. XXXI. p-Anisonium and methylphenonium ion-formation via aryl participation in strong acid solution

1967 ◽  
Vol 89 (20) ◽  
pp. 5259-5265 ◽  
Author(s):  
George A. Olah ◽  
Melvin B. Comisarow ◽  
Eli. Namanworth ◽  
Brian G. Ramsey
Keyword(s):  
Acid Solution ◽  
Strong Acid ◽  
Ion Formation ◽  
Carbonium Ions ◽  
Aryl Participation

An Investigation of Gaseous α-Halogenated Carbocations and Isomeric Halonium, Halenium, and Allylhalonium Ions

2003 ◽  
Vol 56 (5) ◽  
pp. 437 ◽  
Author(s):  
Robert W. Holman ◽  
Jennifer Davis ◽  
Amy Walstrom ◽  
Michelle McCombs ◽  
Gina Jackson ◽  
...  
Keyword(s):  
Gas Phase ◽  
Halogen Atom ◽  
Mass Spectrometric ◽  
Recent Theory ◽  
Tandem Mass ◽  
Carbenium Ions ◽  
Ion Formation ◽  
Tandem Mass Spectrometric ◽  
Ion Species ◽  
Halonium Ion

We investigated with tandem mass spectrometric methods (MS/MS) the nature and extent of stabilization of gas-phase alkyl, vinyl and 2-allyl carbenium ions caused by halogen participation of neighboring chlorine and bromine atoms. The extent of halogen atom stabilization is greatest for alkyl ions, followed closely by that for vinyl ions, and is significantly less for the 2-halosubstituted allyl ions. The data is consistent with bridged halonium ion formation in alkyl systems and bridged halenium ion formation in vinyl systems. Our results for the 2-chloro allyl system are in accord with an earlier NMR interpretation rather than with recent theory, indicating that a bridged allyl halonium ion species is involved.

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