Stereoselective Nitration of Olefins with tBuONO and TEMPO: Direct Access to Nitroolefins under Metal-free Conditions

Soham Maity, Togati Naveen, Upendra Sharma and Debabrata Maiti*

*Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076, India, Email: dmaitiiitb.ac.in

S. Maity, T. Naveen, U. Sharma, D. Maiti, Org. Lett., 2013, 15, 3384-3387.

DOI: 10.1021/ol401426p

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Abstract

A wide range of olefins with diverse functionalities has been nitrated in synthetically useful yields in a single step under metal-free conditions. This transformation is operationally simple and exhibits excellent E-selectivity. Furthermore, site selective nitration in a complex setup makes this method advantageous.

see article for more examples

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A Predictably Selective Nitration of Olefin with Fe(NO₃)₃ and TEMPO

T. Naveen, S. Maity, U. Sharma, D. Maiti, J. Org. Chem., 2013, 78, 5949-5954.

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Key Words

Nitro Compounds, TEMPO, tert-butyl nitrite

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ID: J54-Y2013