Intramolecular cycloaddition reactions involving nitrile sulphides
โ 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
No coin nor oath required. For personal study only.
โฆ 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.
๐ SIMILAR VOLUMES
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