Exclusive peri-selective and regio- and stereoselective cycloaddition reactions of benzocycloheptadienones
β Scribed by Sarkar, Subrata; Saha, Goutam; Ghosh, Subrata
- Book ID
- 127395391
- Publisher
- American Chemical Society
- Year
- 1992
- Tongue
- English
- Weight
- 449 KB
- Volume
- 57
- Category
- Article
- ISSN
- 0022-3263
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2,4-Dioxopentane-3-thione 1a reacts as an enophile with ethers or allenes as ene counterparts, the formation of the thiophilic adduct is followed by a fast cycloaddition reaction various allyl derivatives affording thiophilic ene adducts as single regioisomers with high (E) stereoselectivity. Using
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