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Na (MeOCH2CH2O)2AlH2 REDAL OH 48 REDUCTIONS 49 Chem. Rev. 1986, 86, 763 Org. Rxn. 1951, 6, 469. Lithium Aluminium Hydride LiAlH4 (LAH) - very powerful reducing agent - used as a suspension in ether or THF - Reduces carbonyl, carboxylic acids and esters to alcohols - Reduces nitrile, amides and aryl nitro groups to amines - opens epoxides - reduces C-X bonds to C-H - reduces acetylenic alcohols trans-allylic alcohols LAH OH R OH R H2N LAH, THF N H NH 2 H2N (62%) NH 2 N H NH 2 Lindlar/ H2 H2N O N H HO CO 2Me OH LAH, THF, ↑↓ TL 1988, 29 , 2793.

Rxn. O. House Modern Synthetic Reactions, 2nd edition) R COCl R CHO R NO 2 R NH 2 R R' R R CH 2-OH R CHO R CH CH R CH 2 CH 2 R' R' O R HO H R' Ar R' R O R R' Ar CH 3 + HO R R CH 2 NH 2 R C N O R CH 2-OH R + HO R' OR' O R' R R N CH 2 R' N R' R' requires high temperature & pressure R CO 2- Na+ no reaction Raney Nickel Desulfuriztion , Reviews: Org. Rxn. 1962, 12, 356; Chem. Rev. 1962, 62, 347. R R S R Raney Nickel R H R H (CH 2)n O R S 31 REDUCTIONS O O O O O HO 32 O HO Raney Nickel JOC 1987, 52, 3346 EtOH (74%) H S H S Homogeneous Catalytic Hydrogenation - catalyst is soluble in the reaction medium - catalyst not "poisoned" by sulfur - very sensitive to steric effects - terminal olefins faster than internal; cis olefins faster than trans R R > > R R R R > R R R > R R >> R R R - (Ph3P)3RhCl (Wilkinson's Catalyst); [R3P Ir(COD)py]+ PF6- (Crabtree's Catalyst) (Ph3P)3RhCl, H2 OH OH JOC 1992, 57, 2767 C 6H6 (92%) Directed Hydrogenation Review: Angew.

1 1981, 2055 t-Butyldiphenylsilyl Ether tBuPh2Si-OR TBDPS-OR ∑-OR - stable to acid and base - selective for 1° alcohols - Me3Si- and iPr 3Si groups can be selectively removed in the presence of TBS or TBDPS groups. - TBS can be selectively removed in the presence of TBDPS by acid hydrolysis. TL 1989, 30 , 19 PROTECTING GROUPS cleavage - F- Fluoride sources: - nBu 4NF (basic reagent) HF / H2O /CH3CN HF•pyridine SiF4. CH2Cl2 TL 1979, 3981. Synthesis 1986, 453 TL 1992, 33 , 2289 Me O Si OH tBu Me JOC 1981, 46 ,1506 TL 1989, 30 , 19.

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Advanced Organic Reactions by Rizzo C.J.

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