By Rizzo C.J.
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Additional resources for Advanced Organic Reactions
Alkyl Borohydrides Selectrides M + HB 3 M + = Li (L-selectride) K (K-selectride) LS-selectride Li + HB 3 - hindered reducing agent increased selectivity based on steric considerations CO 2H O CO 2H OH L-selectride THF JACS 1971, 93, 1491 R R HO HO OH OH REDUCTIONS 45 - selective 1,4-reductions of α,β-unsaturated carbonyl cmpds. JOC 1975, 40 , 146; JOC 1976, 41 , 2194 O O K-selectride, THF (99%) - 1,4-reduction generates an enolate which can be subsequently alkylated. O O a) K-selectride, THF b) Br K+ HBPh3 Syn.
Comprehensive Organic Synthesis 1991, vol. 8, 811 Tetrahedron 1992, 48, 2529 W. B. Motherwell, D. Crich Free Radical Chain Reactions in Organic Synthesis (Academic Press: 1992) - free radical reduction of halide, thio ethers, xanthates, thionocarbanates by a radical chain mechanism. nBu3Sn-H, AIBN Ph-CH3 ↑↓ R3C-H R3C-X S X= -Cl, -Br, -I, -SPh, S S Ph , O O Barton-McCombie Reduction JCS P1 1975, 1574 R3C-X → R3C-H N N CN SMe , O CN AIBN N N X= -OC(=S)-SMe, -OC(=S)-Im, -OC(=S)Ph O O O O HO NaH, imidazole, THF, CS2, MeI O O O O O O O nBu3SnH, AIBN PhCH3, reflux O O O O (85%) O SMe S Xanthate R R Cl a) Ph nBu3SnH, AIBN PhCH3, reflux NMe2 , THF + S b) H2S, pyridine HO (73%) Ph (90%) R O Thionobenzoates S Ph O O O HO AcHN OBn N N N (CH2Cl)2 59% Ph N N N O O O O AcHN OBn S Thiocarbonyl Imidazolides nBu3SnH, AIBN PhCH3, reflux (57%) Ph O O AcHN O OBn REDUCTIONS - Cyclic Thionocarbonates: deoxygenation of 1,2- and 1,3-diols to alcohols 55 S OH N O HO MeO MeO S N O O MeO N N HO O JCS P1 1977, 1718 MeO (61%) MeO OMe nBu3SnH, AIBN PhCH3, reflux O MeO OMe OMe - Thionocarbonate Modification (Robbins) JACS 1981, 103 , 932; JACS 1983, 105 , 4059.
1° alcohols give a mixture of aldehydes and carboxylic acids. - Insertion into 3° C-H bonds to give R3C-OH DCC-H2O2 JOC 1998, 63, 2564 R R N C N R H2O2, MeOH H N R N C H O O O O R R + H N R C N R H REDUCTIONS Carey & Sundberg Chapter 5 problems: 1a,b,c,d,f,h,j; 2; 3a-g, n,o; 4b,j,k,l; 9; 11; Smith: Chapter 4 March: Chapter 19 30 Reductions 1. Hydrogenation 2. Boron Reagents 3. Aluminium Reagents 4. Tin Hydrides 5. Silanes 6. Dissolving Metal Reductions Hydrogenations Heterogeneous Catalytic Hydrogenation Transition metals absorbed onto a solid support metal: Pd, Pt, Ni, Rh support: Carbon, alumina, silica solvent: EtOH, EtOAc, Et2O, hexanes, etc.