Journal
ORGANIC LETTERS
Volume 15, Issue 15, Pages 3954-3957Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol401735v
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Funding
- National Science Foundation [CHE 0955972]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0955972] Funding Source: National Science Foundation
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An efficient nitration of silyl allenes with nitrogen dioxide radical, generated from NaNO2 and AcOH, to form alpha-nitro-alpha,beta-unsaturated silyl oximes has been developed. A similar nitration could be achieved by using Fe(NO3)(3)center dot 9H(2)O and FeCl3 center dot 6H(2)O, but different from the regioselective oxime formation, two regioisomeric chloride-trapped products were isolated with varying ratios depending on the steric bulk of the silyl group. A novel ring-closure reaction of alpha-nitro-alpha,beta-unsaturated silyl oximes upon treating with TBAF to form isooxazolidinone derivatives was also developed.
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