Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 17, Pages 2617-2625Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202000149
Keywords
tert-Butyl nitrite; Oxidative nitration; Nitro alkenes; Internal alkenes; beta-Attack
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Funding
- Department of Science and Technology (DST/SERB) [EMR/2016/007042]
- CSIR [0333/NS-EMRII]
- MHRD, New Delhi [5-5/2014-TS-VII (SB/S1/OC-53/2013)]
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In an oxygen atmosphere tert-butyl nitrite (TBN) reacts with unsymmetrical internal benzylic alkenes giving nitro-nitratosation product exclusively. The gamma-diaryl-substituted styrenes provided better yields compared to gamma-alkyl-aryl-substituted styrenes. The higher yields for the former type of substrates is possibly dictated by the additional stability of benzylic radical due to the anchimeric assistance imparted by the gamma-substituted phenyl ring. During oxidative nitration, the nitro (NO2) group adds at the non-benzylic site, whereas the nitrato group (ONO2) is attached at the relatively stable benzylic position. Under similar reaction conditions, alpha,beta-unsaturated carboxylic acids, afforded nitroalkenes as the sole product.
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