Thermal rearrangement of N-benzylanilinium hexafluoroantimonates

We prepared p-substituted N-benzylanilinium hexafluoroantimonates, known cationic initiators, and examined their thermal reaction. The thermal reaction produced 2- or 4-benzylanilinium salts as the major products, which resulted from the rearrangement of the benzyl group. The reaction proceeded at l...

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 42; pp. 7485 - 7488
Main Authors Park, Jeongkyu, Shin, Jung-Hyu, Lee, Changjin
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.10.1999
Elsevier
Subjects
benzyl migration
Chemistry
Chemistry, Organic
N-benzylanilinium hexafluoroantimonates
Physical Sciences
rearrangement
Science & Technology
benzyl migration
rearrangement
N-benzylanilinium hexafluoroantimonates
SULFONIUM SALTS
SOMMELET-HAUSER REARRANGEMENT
INITIATORS
CATIONIC POLYMERIZATION
CATALYSTS
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Summary:We prepared p-substituted N-benzylanilinium hexafluoroantimonates, known cationic initiators, and examined their thermal reaction. The thermal reaction produced 2- or 4-benzylanilinium salts as the major products, which resulted from the rearrangement of the benzyl group. The reaction proceeded at lower temperature with higher yield when the substituent in the benzyl group was electron donating. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01546-4