water; fluorine in dichloromethane; acetonitrile T=20°C; 0.5 h; Inert atmosphereFlow reactor;

sodium nitrite in N,N-dimethyl-formamide T=0°C;

tetradecyl(trihexyl)phosphonium bistriflimide; sodium nitrite in water T=90°C; 6 h;

water; fluorine in dichloromethane; acetonitrile T=20°C; 1 h; Inert atmosphereFlow reactor;

poly(N-butyl-4-vinylpyridinium)nitrite in hexane T=20°C; 72 h;

2,3,11,12-dicyclohexano-1,4,7,10,13,16-hexaoxacyclo-octadecane; KNO2 T=70°C; 5 h; Yield given;

T=190°C; P=29420.3 Torr;

1.1: 82 percent / TBAF / dimethylformamide / 24 h / 23 °C 2.1: 80 percent / DCC; CuCl / acetonitrile / 18 h / 60 °C 3.1: 50 percent / Zn; AcOH / tetrahydrofuran / 0.25 h / 0 °C 4.1: 77 percent / CAN; HNO3 / ethanol / -45 °C 5.1: 98 percent / 4 N HCl / tetrahydrofuran / 23 °C 6.1: 60 percent / aq. CsCO3 / methanol; dimethylformamide / 23 °C 7.1: Me4NB(OAc)3H / acetic acid; acetonitrile / 24 h / -40 °C 7.2: 96 percent / 2,6-lutidine / CH2Cl2 / 2.5 h / -78 °C 8.1: 99 percent / H2 / Pd(OH)2 / ethyl acetate; methanol / 23 °C 9.1: 74 percent / PhSO2Cl; pyridine / 48 h / 0 °C 10.1: 70 percent / TBAF; AcOH / tetrahydrofuran / 4 h / 0 °C View Scheme

1.1: 82 percent / TBAF / dimethylformamide / 24 h / 23 °C 2.1: 80 percent / DCC; CuCl / acetonitrile / 18 h / 60 °C 3.1: 50 percent / Zn; AcOH / tetrahydrofuran / 0.25 h / 0 °C 4.1: 77 percent / CAN; HNO3 / ethanol / -45 °C 5.1: 98 percent / 4 N HCl / tetrahydrofuran / 23 °C 6.1: 60 percent / aq. CsCO3 / methanol; dimethylformamide / 23 °C 7.1: Me4NB(OAc)3H / acetic acid; acetonitrile / 24 h / -40 °C 7.2: 96 percent / 2,6-lutidine / CH2Cl2 / 2.5 h / -78 °C 8.1: 99 percent / H2 / Pd(OH)2 / ethyl acetate; methanol / 23 °C 9.1: 74 percent / PhSO2Cl; pyridine / 48 h / 0 °C 10.1: 70 percent / TBAF; AcOH / tetrahydrofuran / 4 h / 0 °C 11.1: 90 percent / PPh3; DIAD / tetrahydrofuran / 23 °C View Scheme

Fe(acac)3; 1,1,3,3-tetramethyldisiloxane in tetrahydrofuran T=60°C; Sealed tubeInert atmosphere;