An improved method for preparation of nitrile oxides from nitroalkanes for in situ dipolar cycloadditions

Yochai Basel, Alfred Hassner

Research output: Contribution to journalArticlepeer-review

106 Scopus citations

Abstract

A new method has been found for generation of nitrile oxides in situ from nitroalkanes under mild conditions. Thus, reaction of nitroalkanes 1 with di-tert-butyl dicarbonate (2) and 4-dimethylaminopyridine (3) as catalyst in the presence of dipolarophiles at room temperature afforded cycloadducts (e.g. 5, 6, and 7) in improved yields compared to known methods. Solvent effects were also noted.

Original languageEnglish
Pages (from-to)309-312
Number of pages4
JournalSynthesis
Issue number3
DOIs
StatePublished - 1997

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