D. A. Evans The Nitro Function as a Leaving Group Chem 206 NO2 As a Leaving Group CO2Et Representative examples: O2 N-C(+) (+) No R McMurry etal. Chem Comm. 1971 488-489. O2N R2N SPh Bakuzis etal. Tetrahedron Lett. 1978 2371. O2M 6y Pd(PPh3) DBU I NO2 Nao SPh Pd(PPh3)3 O2N-C-C CO2EtN O O CH R R Nu CH R R Me Me SPh NO2 NO2 Ph SiMe3 SnCl4 NO2 N H Pd(PPh3 )3 NaCH(CO2Me)2 NaO2SPh Pd(PPh3 )3 Pd(PPh3 )3 TiCl4 O2N C SO2Ph Ph Me Me SPh CH(CO2Me)2 N(CH2)5 O N O O2N C C MeO CO2Et NO2 R3N CO2Et NO2 O2N C C O CO2Et CO2Et NO2 CO2Et NO2 O R2NH –NO2 – N O CO2Et NO2 R2NH H3O + DBU O2N C C O2N C C O CO2Et NO2 NO2 MeO CO2Et MeO CO2Et –NO2 – CO2Et O O2N C C D. A. Evans The Nitro Function as a Leaving Group Chem 206 –NO2 As a Leaving Group Representative examples: (+) – + Nu(–) + NO2 – 74% 65% + (+) (+) McMurry etal. Chem Comm. 1971 488-489. (+) (+) + (+) (+) Danishefsky etal. JACS 1978, 100, 2918. (+) (+) (–) (+) Bakuzis etal. Tetrahedron Lett. 1978 2371. (+) (–) (+) (+)