TY - JOUR
T1 - Investigation of O-Sulfonylation-promoted Heterolytic NO Bond Cleavage of Amidoximes and Ketoximes
AU - Hsieh, Tsung Han
AU - Liao, Pen Yuan
AU - Liu, Yu Ting
AU - Wang, Chien Hong
AU - Lin, Chia Chi
AU - Chien, Tun Cheng
N1 - Funding Information:
This work was supported by Research Grants MOST 105-2113-M-003-003-and MOST 104-2113-M-003-001-from Ministry of Science and Technology, Taiwan.
Publisher Copyright:
© 2017 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Copyright:
Copyright 2018 Elsevier B.V., All rights reserved.
PY - 2018/3
Y1 - 2018/3
N2 - Two different reaction pathways were observed in the sulfonylation of N-phenylbenzamidoximes. The reaction with o-NsCl at a heating temperature gave N,N′-diphenylureas via Tiemann rearrangement, while the reaction with Ts2O at a lower temperature formed 2-phenylbenzimidazoles via intramolecular electrophilic aromatic substitution. When the amide nitrogen was replaced with carbon substituents, oxime derivatives of benzoins and benzils underwent Beckmann fragmentation reactions upon sulfonylation, whereas sulfonylation of 2-phenylacetophenone oxime afforded exclusively the Beckmann rearrangement adduct.
AB - Two different reaction pathways were observed in the sulfonylation of N-phenylbenzamidoximes. The reaction with o-NsCl at a heating temperature gave N,N′-diphenylureas via Tiemann rearrangement, while the reaction with Ts2O at a lower temperature formed 2-phenylbenzimidazoles via intramolecular electrophilic aromatic substitution. When the amide nitrogen was replaced with carbon substituents, oxime derivatives of benzoins and benzils underwent Beckmann fragmentation reactions upon sulfonylation, whereas sulfonylation of 2-phenylacetophenone oxime afforded exclusively the Beckmann rearrangement adduct.
KW - Beckmann fragmentation
KW - Beckmann rearrangement
KW - Electrophilic aromatic substitution
KW - Tiemann rearrangement
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UR - http://www.mendeley.com/research/investigation-osulfonylationpromoted-heterolytic-bond-cleavage-amidoximes-ketoximes
U2 - 10.1002/jccs.201700104
DO - 10.1002/jccs.201700104
M3 - Article
AN - SCOPUS:85030529716
VL - 65
SP - 325
EP - 330
JO - Journal of the Chinese Chemical Society
JF - Journal of the Chinese Chemical Society
SN - 0009-4536
IS - 3
ER -