Activation of nitriles by hydrogen bonding in cycloadditions with nitrile oxides
โ Scribed by Antonino Corsaro; Ugo Chiacchio; Pierluigi Caramella; Giovanni Purrello
- Book ID
- 112127522
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1984
- Tongue
- English
- Weight
- 291 KB
- Volume
- 21
- Category
- Article
- ISSN
- 0022-152X
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๐ SIMILAR VOLUMES
The reaction of 0-trimethylsilyl a-bromo aldoximes with unsaturated alcohols produces oximino ethers which can be readily oxidized with sodium hypochlorite. The transient nitrile oxide intermediate formed undergoes spontaneous cyclization affording fused isoxazolines. MM2 calculations help rationali
l%e i&mwMms 2a.2b and 8 obtained from &rile oxide cycloadditions to cyclohex-2-eame 10 and its analogues lb and 'I meted with nickel peroxide to give the imxamks 3a,3b and 9. In contrast, the cme-spoIldillg 2hromocyclohex-2a ~4band18,prepandby~ndthecarespomdiagalLenesla,lb and 1, m&went nitrile oxid