Advanced Organic Reactions by Rizzo C.J.

By Rizzo C.J.

Show description

Read or Download Advanced Organic Reactions PDF

Best organic chemistry books

Volume 3, The Organic Chemistry of Drug Synthesis

The vintage reference at the synthesis of medicinal brokers --now thoroughly up to date The 7th quantity within the definitive sequence that gives a short but thorough evaluate of the unreal routes used to entry particular classesof healing brokers, this quantity covers nearly 220 new non-proprietary drug entities brought because the ebook of quantity 6.

Restoration of contaminated aquifers: petroleum hydrocarbons and organic compounds

The second one variation of recovery of infected Aquifers: Petroleum Hydrocarbons and natural Compounds accommodates the most recent advances in in-situ remediation and traditional attenuation, and continues the excellent, obtainable constitution that made the 1st version a vintage. the hot version broadens the scope of the 1st via studying all sorts of hydrocarbon illness.

Palladium Reagents and Catalysts: Innovations in Organic Synthesis

Lately, there was loads of growth in organopalladium chemistry. a variety of new artificial equipment were built, which use palladium reagents both as catalysts or as stoichiometric reagents. this article offers man made natural chemists with a well timed perception into present learn on palladium reagents.

Additional resources for Advanced Organic Reactions

Example text

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.

Download PDF sample

Rated 4.39 of 5 – based on 6 votes