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Nitroalkane synthesis. A convenient method for aldehyde reductive nitromethylation

✍ Scribed by Robert H. Wollenberg; S.J. Miller

Publisher: Elsevier Science
Year: 1978
Tongue: French
Weight: 233 KB
Volume: 19
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)85598-2

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✦ Synopsis

Our interest in the intramolecular cycloaddition of nitrile oxides with olefins as a tool for natural product synthesis prompts this report of a simple one-pot synthesis of nitroalkanes from aldehydes. Nitroalkanes are useful precursors to these dipolar intermediates.

1 Further, the considerable progress in synthetic methodologies for the conversion of a nitro functional group to other functionality under mild conditions, particularly the carbonyl' and amino3 groups, suggests that formation of nitroalkanes will become increasingly more important. Methods which proceed under conditions generally suitable to complex natural product synthesis will be especially useful. 4

Nitroalkanes are readily deprotonated to their nitronates 1; 1,2 however, these reagents

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