Synthesis

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

Y Basel, A Hassner

Index: Basel, Yochai; Hassner, Alfred Synthesis, 1997 , # 3 p. 309 - 312

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Citation Number: 71

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 aflorded cycloadducts (eg 5, 6, and 7) in im-proved yields compared to known methods. Solvent effects were also noted.