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Carbonyl ylide formation from the rhodium (II) acetate catalyzed reaction of a α-diazoketone

✍ Scribed by Albert Padwa; Paul D. Stull

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
263 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

Reaction of the a-diazoketone derived from 7-carboxyphthalide with rhodium acetate results in an internal cyclization to give a six-ring carbonyl ylide which is subsequently converted to 7carbomethoxyphthalide.

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Treatment of 1-diazoalkanediones with rhodium (II) acetate results in cyclization of the intermediate rhodium carbenoid to give a cyclic carbonyl ylide which readily undergoes bimolecular dipolar cycloaddition with various dipolarophiles. a-Diazoketones are valuable synthetic intermediates, with con

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