tert‐Butyl Nitrite Mediated Nitro‐Nitratosation of Internal Alkenes

Abstract

In an oxygen atmosphere tert-butyl nitrite (TBN) reacts with unsymmetrical internal benzylic alkenes giving nitronitratosation product exclusively. The γ-diaryl-substituted styrenes provided better yields compared to γ-alkyl-aryl-substituted styrenes. The higher yields for the former type of substrates is possibly dictated by the additional stability of benzylic [a] B.

Trifunctionalization of CC bonds in vinyl azides to access densely functionalized phenanthridines enabled by the NCS/AgNO2 system

“…In this regard, NO 2 radical-triggered multifunctionalization of alkenes via various nitrating reagents has become a powerful tool for the synthesis of nitro-containing compounds. 6,7 To date, NO 2 radical-involved monofunctionalizations 6 and bifunctionalizations 7 of alkenes have been extensively studied (Scheme 1a). For example, a series of nitrating reagents have been exploited for the monofunctionalization of alkenes with high selectivities.…”