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Ligand effects in the metal catalysed reactions of N-aryldiazoamides: Ylide formation vs. insertion reactions

✍ Scribed by Christopher J Moody; Soyfur Miah; Alexandra M.Z Slawin; Darren J Mansfield; Ian C Richards

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 745 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00525-0

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✦ Synopsis

Diazoamides la and lb were prepared from 2-(O-allyl)-and 2-(S-allyl) anilines 2 respectively. Copper(II) catalysed decomposition of 1 resulted in formation of benzofused heterocycles 7 by [2,3]-rearrangement of the intermediate ylide. Rhodium(II) perfluorbutyramide catalysed reaction, however, gave mainly the indoles 8, 9 whereas rhodium(II) acetate catalysed reaction resulted in a mixture of products, with 13-1actams formed by intramolecular C-H insertion predominating. Catalysed decomposition of N-pyridyl diazoamide 13 gave the stable pyfidinium ylide 14.

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ChemInform Abstract: Ligand Effects in t

ChemInform Abstract: Ligand Effects in the Metal-Catalyzed Reactions of N-Aryldiazoamides: Ylide Formation vs. Insertion Reactions.

✍ C. J. MOODY; S. MIAH; A. M. Z. SLAWIN; D. J. MANSFIELD; I. C. RICHARDS 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 39 KB 👁 2 views

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