Selective Reactions of Azide-Substituted a-Diazo Amides with Olefins and Alcohols Using Rhodium(II) Catalysts

Alwarsamy Jeganathan, Stewart K. Richardson, Rajarathnam S. Mani, Boyd E. Haley, David S. Watt

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

The synthesis and addition of azide-substituted a-diazo amides such as N-(4-azidophenyl)-a-diazoacetamide and N-(4-azido-2-hydroxyphenyl)-α-diazoacetamide to olefins and alcohols using either rhodium(II) acetate or preferably rhodium(II) pivalate provided cyclopropanecarboxamides and a-alkoxy amides, respectively, without disrupting the azide functionality. These azide-bearing a-diazo amides are potentially useful in the preparation of photoaffinity cross-linking reagents for studying the mechanism of action of natural products.

Original languageEnglish
Pages (from-to)5362-5367
Number of pages6
JournalJournal of Organic Chemistry
Volume51
Issue number26
DOIs
StatePublished - 1986

ASJC Scopus subject areas

  • Organic Chemistry

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