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A new conversion of primary nitro compounds into nitriles

✍ Scribed by Laurent El Kaim; Ariane Gacon

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
157 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The reaction ofprima~ nitro compounds with isocyanides and isocyanates in the pmsen~ Β’f a base leads to a new preparation ff nitriles. The reaction probably proceeds through the in situ formation of a nitrile oxide followed by a fast oxygen transfer with the isocyanide. Combined with the Knovemgel addition of nitromethane to cyclic ketone, this reaction brings a highly effective regioselective formation of cyclic o~-~ unsaturated nitriles.

πŸ“œ SIMILAR VOLUMES

New synthetic β€˜tricks’. Direct conversio
New synthetic β€˜tricks’. Direct conversion of nitro compounds to nitriles
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Treatment of primary nitro groups, in CH2Cl2 at 0 "c. with Sn(SPhM. R3P. and DEAD affords quickly and abnost quantitatively the corresponding n&riles. in a combined process of deoxygenation and delrydration. The same restdt can be obtained, although not so rapidly. uing only R3P (2 eqtdv.) ond DEAD

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New synthetic β€˜tricks’. A novel one-pot
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Two tin@) complexes, Sn(SPhh-and Sn(C4H406)g2-. besides NaHSo3. are involved in a procedure developed for the rapid transfmation at pH 5-6 of R-CHZ-NO2 into R-CHOH-S03Na. from which the de&d aldehydes have been isdated in 80-91% overall yields. llms, a new ahemative to the Nef maction is now in hand