Hydride abstraction in FSO3H and other media - an electron transfer mechanism

✍ Scribed by Richard M. Pagni; Paul A. Bouis; Paul Easley

• Book ID: 104215114
• Publisher: Elsevier Science
• Year: 1975
• Tongue: French
• Weight: 203 KB
• Volume: 16
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)75210-5

✦ Synopsis

Fluorosulfonic acid (FSO&I) and mixtures of FSOsH and SbF. are among the very strongest acids known, 1 and numerous reactions occur in them that have no counterpart in other acids or solvents.* For example, treatment of saturated alkanes, such as isobutane, with FSOsH-SbF. generates the corresponding carbenium ion by a process which is formally a hydride abstraction. 3 Some hydrogen is also produced in the reactions. Recently we reported4 that cycloheptatriene (1) and phenalene (2) are oxidized in FSOsH, both in the presence and absence of SbF ,, to the corresponding carbenium ion. FSOsH HaSO* CF?rCOOH CE.CN PER+ NO NO No No -14a No No No No -13.3a Triphenylmethsne (1) No 7E-Benz[d,e]anthracene @) Yes 1,2,5,6-Dibenzcycloheptatriene (2) Yes Eanthene (10) No -Thioxanthene (11) Yes -Phenalene (2) Yes Tris(E_Anisyl)methane (12) No -Cycloheptatriene (f) Yes No Yes Yes No Yese Yes No Yes