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Efficient and Stereoselective Nitration of Mono- And Disubstituted Olefins With AgNO2 and TEMPO

Soham Maity, Srimanta Manna, Sujoy Rana, Togati Naveen, Arijit Mallick, Debabrata Maiti

J Am Chem Soc. 2013 Mar 6;135(9):3355-8.

PMID: 23406020

Abstract:

Nitroolefin is a common and versatile reagent. Its synthesis from olefin is generally limited by the formation of mixture of cis and trans compounds. Here we report that silver nitrite (AgNO2) along with TEMPO can promote the regio- and stereoselective nitration of a broad range of olefins. This work discloses a new and efficient approach wherein starting from olefin, nitroalkane radical formation and subsequent transformations lead to the desired nitroolefin in a stereoselective manner.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP7783995 Silver nitrite Silver nitrite 7783-99-5 Price
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