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Isolation of the Quinone Mono O,S ‐Acetal Intermediates of the Aromatic Pummerer‐Type Rearrangement of p ‐Sulfinylphenols with 1‐Ethoxyvinyl Esters
Author(s) -
Kita Yasuyuki,
Tekeda Yoshifumi,
Matsugi Masato,
Iio Kiyosei,
Gotanda Kentoku,
Murata Kenji,
Akai Shuji
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199715291
Subject(s) - acetal , quinone , pummerer rearrangement , chemistry , stereochemistry , organic chemistry , catalysis , acetic anhydride
A versatile synthetic building block and evidence for the mechanism of the Pummerer‐type rearrangement have been obtained in the form of the acetal intermediate B , isolated in the reaction of p ‐sulfinylphenols 1 to p ‐quinones 2 induced by acid anhydrides. Thus, a method is now also available for the efficient preparation of quinone monoacetals under nonoxidative conditions.