Tetrahedron p. 8025 - 8032 (2000)
Update date:2022-08-03
Topics:
Grigg
Rankovic
Thoroughgood
Acyclic oxyiminium ion generation from secondary hydroxylamines (4a,b and 6a,b) and formaldehyde in the presence of acetic acid is reported. Trapping these electrophiles with 2-methyl furan, pyrrole or indole affords a series of novel O-benzyl tertiary hydroxylamines in good to excellent yield. Benzotriazole mediated synthetic methodology has also been successfully developed to generate oxyiminium ions which react with Grignard reagents, to give novel O-benzyl tertiary hydroxylamines. (C) 2000 Elsevier Science Ltd.
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