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α-Chlor-nitrone I: Darstellung und Ag+-induzierte Reaktion mit Olefinen. Über synthetische Methoden, 5. (vorläufige) Mitteilung

✍ Scribed by U. M. Kempe; T. K. Das Gupta; K. Blatt; P. Gygax; Dorothee Felix; A. Eschenmoser

Publisher
John Wiley and Sons
Year
1972
Tongue
German
Weight
766 KB
Volume
55
Category
Article
ISSN
0018-019X

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✦ Synopsis

TJber synthetischc Methoden, 5. (vorlaufige) Mitteilung l) Suvnmuvy. Organic synthcsis may be said t o be in need of eaofihiles, 1.e. rcagcnts that would uiidcrgo cycloatldition rcactions with any isolated olefinic double bond, in contrast t o most of thc classical Diels-Alder or 1,3-dipolar addition rcagcnts which, as a rule, require activated olcfins in ordcr t o participatc smoothly in cycloaddition processes. This paper introduces a-chloronitrones as precursors of a new class of such rcagents; they undergo an Ag+-induced reaction with unactivated olefins with great case to give products considered to result from 1,4-cycloadditions o f N-alkyl-N-vinyl-nitrosonium ions t o thc carhon-carbon double bond (see scheme 2). This process is believcd to have a number of synthetic applications, two of thctn bcing illustrated in two subscqueiit communications.

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