Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 4, Pages 1244-1250Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo902618e
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Funding
- NSERC (Canada)
- Canada Research Chair Program
- Canada Foundation for Innovation
- Universite de Montreal
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The formation of a new phosphate carbenoid (n-BuO)(2)P(O)OZnCH2I and its application in organozinc-mediated reactions is described. This carbenoid undergoes very slow degradation in solution and can be stored for several weeks at -20 degrees C. Its reactivity was tested with many representative alkenes and was determined to be a powerful cyclopropanating reagent, giving the corresponding cyclopropanes in 72-99% yield. The use of this carbenoid in the chain extension of 1,3-diketones and [2,3]-sigmatropic rearrangement reactions is also described.
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