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Eine Abfangmethode zum Nachweis kurzlebiger Carbenium‐Ionen in stark sauren Reaktionsmedien
Author(s) -
Bosshard H.,
Baumann M. E.,
Schetty G.
Publication year - 1970
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19700530603
Subject(s) - chemistry , carbenium ion , sulfonium , pinacol , ion , medicinal chemistry , photochemistry , alcohol , organic chemistry , catalysis , salt (chemistry)
In a new approach, unstable carbenium ions produced in strong protic media could be trapped by thioethers yielding sulfonium compounds. The method has successfully been applied to the rearrangement reactions of sec ‐butyl alcohol and pinacol, where carbenium ions could be trapped before their rearrangement. In the case of the pinacol‐pinacon rearrangement the carbenium ion 13 has already been discussed but for the first time its existence is proved. Since compound 16 has been found, a new mechanism for the pinacol‐pinacon rearrangement is postulated starting with diprotonated pinacol.