KF, 18-crown-6 L = Br. OTS, OX LiAIDA (LiAIHA) AIBN Buz SnH M = Li, MgBr, Na M-=- NaCN KCN DMSO, A 18-crown-6 LICI, DMF BnBuzNCI [= OTS acetone DMSO LiBr, acetone NaBr L = OTS L = CI PR'3 (NR"3) L=1 Nal, acetone L = Br RSL H2O 1. AcO KO2 2. KOH DMSO : P(OET)3, A L = CI, Br, 1 R'ONa AroNa THE DMSO L = CI, Br, 1 OSO2R', OTE, OMs, OTS, OBS, ONS AcOHRANOAC L = OBS, OTS 1. 1. 2Ag CN 1. TMSON 2. KCN 2, TBAP (NH2)2Cs AcSK or 2. OH"/H30* NASH AgNO2 NaNO2 DMF TsNH 2, KOH DMF 1. K Phthalimide 2. NH2NH2 H2O ENEN I DMSO, A 18-crown-6 Nang NaSOR ArsNa DMSO, A R'SNa KSCN