TY - JOUR
T1 - Selective Reactions of Azide-Substituted a-Diazo Amides with Olefins and Alcohols Using Rhodium(II) Catalysts
AU - Jeganathan, Alwarsamy
AU - Richardson, Stewart K.
AU - Mani, Rajarathnam S.
AU - Haley, Boyd E.
AU - Watt, David S.
PY - 1986
Y1 - 1986
N2 - 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.
AB - 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.
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U2 - 10.1021/jo00376a057
DO - 10.1021/jo00376a057
M3 - Article
AN - SCOPUS:33644889303
SN - 0022-3263
VL - 51
SP - 5362
EP - 5367
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 26
ER -