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ChemInform Abstract: Unsaturated Nitriles: Precursors for a Domino Ozonolysis—Aldol Synthesis of Oxonitriles.

✍ Scribed by Fraser F. Fleming; Adrian Huang; Vaqar A. Sharief; Yifang Pu

Publisher
John Wiley and Sons
Year
2010
Weight
36 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Unsaturated Nitriles: Precursors for a Domino Ozonolysis-Aldol Synthesis of Oxonitriles.

-A highly efficient one-pot synthesis of six-and seven-membered oxonitriles (II) and (IV) is achieved by tandem ozonolysis-aldol reaction of unsaturated nitriles (I) and (III). This reaction sequence represents a new method of ring expansion. The synthesis of cyclic five-membered oxonitriles (VIII) and (IX) or more substituted six-membered oxonitriles such as (XII) involving the tandem ozonolysis-aldol sequence is achieved starting from ω-alkenyl esters (V) or (X), many of which are commercially available. -(FLEMING,

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