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Intramolecular cycloaddition reactions involving nitrile sulphides

โœ Scribed by Peter A. Brownsort; R.Michael Paton; Alan G. Sutherland


Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
189 KB
Volume
26
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


ortho-(Phenylpropioloxy)benzonitrile sulphide, generated in situ by thermal decarboxylation of the oxathiazolone Cl), undergoes intramolecular 1,3-dipolar cycloaddition forming the chromenoisothiazole (48); ortho-cinnamoylbenzonitrile sulphides also yield (4), together with nitrile. chromenoquinoline and aminochromene by-products.


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Intramolecular nitrile oxide cycloaddition to functionalized furans occurs with complete regiochemical control but low diastereoselectivity. The poor reactivity of furan as 2 3Z component in the 1,3-dipolar cycloaddition with nitrile oxide' greatly limited its practical use in this reaction. 2,3 Thi