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Title: Studies in amine oxide rearrangement: Meisenheimer rearrangement of <i>m</i>-substituted tertiary amine oxides
Authors: Majumdar, K C
Roy, B
Basu, P K
Biswas, P
Keywords: Meisenheimer rearrangement
<i style="">m</i>-substituted allylalkylaryl amines
<i style="">m</i>-CPBA
allene intermediate
amine oxide rearrangement
Issue Date: Mar-2006
Publisher: CSIR
Series/Report no.: <b>Int</b>.<b>Cl</b>.<b><sup>7</sup> C 07 D</b>
Abstract: A number of N-substituted but-2-ynyl, allyl and 4-aryloxy-2-butynyl-N-methyl anilines <b style="">2a-c</b>, <b style="">3a-h</b> and <b style="">5d-f</b> have been synthesized in excellent yield. The <i style="">m</i>-substituted allylalkylaryl amines have been then treated with one equivalent of <i style="">m</i>-chloroperoxybenzoic acid (<i style="">m</i>-CPBA) to give products <b style="">9a-h</b> in 80-95% yield. The 4-aryloxy-2-butynyl-N-methyl anilines <b style="">5d-f</b> on treatment with <i style="">m</i>-CPBA proceed through the allene intermediate <b style="">7</b>.
Description: 719-725
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.45B(03) [March 2006]

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