2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene 1 h; Heating;

1: hydroxylamine hydrochloride, pyridine / H2O / 1 h / Ambient temperature 2: CuSO4*5H2O, Et3N, DCC / CH2Cl2 / 2 h / Ambient temperature 3: 32 percent / n-Bu3SnH, AIBN / benzene / 5 h / Heating View Scheme

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene 1 h; Heating;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '7054643', constants.ctx, '0')">pyridinium chlorochromate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />7&nbsp;h;&nbsp;&nbsp;Ambient temperature;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 1.) Mg / 1.) Et₂O, 2.) Et₂O, r.t., 2 d<br />2: 1.) 9-BBN, 2.) 30percent aq. H₂O₂, 6 M aq. NaOH / 1.) THF, r.t., 1 h, 2.) EtOH, r.t., 15 min; 50 deg C, 10 min<br />3: 68 percent / PCC / CH₂Cl₂ / 7 h / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 67 percent / NBS, benzoyl peroxide / CCl₄ / 2 h / Heating<br />2: 1.) Mg / 1.) Et₂O, 2.) Et₂O, r.t., 2 d<br />3: 1.) 9-BBN, 2.) 30percent aq. H₂O₂, 6 M aq. NaOH / 1.) THF, r.t., 1 h, 2.) EtOH, r.t., 15 min; 50 deg C, 10 min<br />4: 68 percent / PCC / CH₂Cl₂ / 7 h / Ambient temperature<br /> <br /> &nbsp;