Fukuyama Group-Group Meeting Cumulative Examination 4/26/2014 Name 1. TBSO Ti(Oi-Pr)4 (cat*) EtMgBr (2 eq.*) CO2Et OTBS THF, 10 °C 1) MsCl, Et3N Et2O, 0 °C TBSO OTBS 2) MgBr2·Et2O CH2Cl2, reflux 73% (3 steps) Br *theoretical amount J. Mulzer et al., Org. Lett., 10, 4701 (2008) 2. 1) 1-hexyne CuI, PdCl2 Ph3P, i-Pr2NEt DMF, rt, 94% PBr3 (2 eq.*) DMF (2 eq.*) C6H7BrO O CHCl3 0 °C to rt 2) Me2NNH2 CHCl3, rt quant. MeO Cr(CO)5 Ph OMe n-Bu THF, reflux Ph 68% 77% * theoretical amount Y. Zhang and J. W. Herndon, Org. Lett., 5, 2043 (2003) J. W. Herndon and H. Wang, J. Org. Chem., 63, 4564 (1998) 4. O H Ph H Ph Ph3P Se TFA CH2Cl2, rt Ph Ph 演習で学ぶ有機反応機構B102（化学同⼈） D. L. J. Clive and C. V. Denyer, J. Chem. Soc., Chem. Commun., 253 (1973) 5. Cl Cl D Ph Ph N D D benzene 220 °C Ph N Ph 41% S. Kagabu et al., J. Chem. Soc., Perkin Trans. 1, 739 (1994) 6. O NH CuCl dicumyl peroxide O N Me C6H5Cl 130 ºC 91% W. Chen et al., Org. Lett., 15, 3326 (2013) 3. (a) Draw the structures of the reagents below. AIBN Meldrum's acid CSI TosMIC DABCO (b) Provide the names in the full lengths. CSA DBU EDCI NBS NMO 演習で学ぶ有機反応機構（化学同⼈）
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