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An efficient and general approach to beta-functionalized ketones.

Organic letters (2007-03-06)
Jingliang Jiao, Larry X Nguyen, Dennis R Patterson, Robert A Flowers
ABSTRACT

[structure: see text]. The oxidation of selected anions (N3-, SCN-, I-, and Br-) by ceric ammonium nitrate (CAN) in the presence of substituted cyclopropyl alcohols provides a novel approach to beta-functionalized ketones. The protocol has a number of advantages including short reaction times, ease of reagent handling, and mild, neutral reaction conditions. Overall, this method provides an alternative pathway to important starting materials and intermediates in organic synthesis.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ammonium cerium(IV) nitrate, ≥99.99% trace metals basis
Sigma-Aldrich
Ammonium cerium(IV) nitrate, JIS special grade, ≥95.0%
Sigma-Aldrich
Ammonium cerium(IV) nitrate, puriss. p.a., ACS reagent, ≥98.5% (RT)
Sigma-Aldrich
Ammonium cerium(IV) nitrate, ≥98% (titration)
Sigma-Aldrich
Ammonium cerium(IV) nitrate, ACS reagent, ≥98.5%