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Twofold Carbon-Carbon Bond Formation by Intra- and Intermolecular Radical Reactions of Aryl Diazonium Salts

✍ Scribed by Jasch, Hannelore; Landais, Yannick; Heinrich, Markus R.

Book ID
120395595
Publisher
John Wiley and Sons
Year
2013
Tongue
English
Weight
383 KB
Volume
19
Category
Article
ISSN
0947-6539

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✦ Synopsis

Cascade reactions: A variety of novel cascade reactions can be performed when the known and well-studied radical 5- or 6-exo-cyclization of an aryl diazonium salt is conducted in the presence of alkenes and further optional scavengers (see scheme).

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Terminal alkenes of the type H 2 C C(OR 1 )X, in which R 1 is a tertiary alkyl or a 1-cyclopropylethyl group and X=Ph, OSiMe 2 Bu t , OEt or H, undergo radical-chain reactions with organic halides R 2 Hal to give carbonyl compounds R 2 CH 2 C( O)X.