By Rizzo C.J.
Read or Download Advanced Organic Reactions PDF
Similar organic chemistry books
An easy-to-use reference resource for all scientists operating with carbohydrates, the Dictionary of Carbohydrates with CD-ROM, moment variation builds at the good fortune of its past variation via supplying a considerably elevated variety of compounds. The presentation is sharpened through a cautious evaluate of present entries.
Enormous advances were made concerning the chemistry of triple-bonded sensible teams because the first quantity during this sequence was once released. This up to date model covers details which has been said over the past 15 years.
Teaches scholars to exploit the language of sythesis at once (utilizing the grammar of synthon and disconnection) instead of translating it into that of natural chemistry.
- Tellurium in Organic Synthesis: Second, Updated and Enlarged Edition
- Heteroatom Manipulation, Volume Volume 6
- Greene's Protective Groups in Organic Synthesis (4th Edition)
- Organic Light-Emitting Diodes: Principles, Characteristics & Processes
- Absorbable and Biodegradable Polymers (Advances in Polymeric Biomaterials)
- Handbook of Organic Food Safety and Quality, 1st Edition
Additional resources for Advanced Organic Reactions
J. Chem. 1970, 48 , 735. Lalancette Reduction 42 NaBH4/ NiCl 2 Chem. Pharm. Bull. 1981, 29 , 1159; Chem. Ber. 1984, 117 , 856. Ar-NO2 → Ar-NH2 Ar-NO → Ar- NH2 R2C=N-OH → R2CH-NH2 NaBH4 / TiCl 4 Synthesis 1980, 695. R-COOH → R-CH2-OH R-COOR' → R-CH2-OH R-CN → R-CH2-NH2 R-CONH2 → R-CH2-NH2 R2C=N-OH → R2CH-NH2 R-SO2-R' → R-S-R' NaBH4 / CeCl 3 Luche Reduction reduced α,β-unsaturated ketones in a 1,2-fashion OH NaBH 4/ CeCl3 R R NaBH 4 R R O OH O R + R R R R R R H R JCSCC 1978, 601 JACS 1978, 100 , 2226 O OH CO 2Me NaBH 4/ CeCl3 C 5H11 CO 2Me MeOH C 5H11 OH OH - selective reduction of ketones in the presence of aldehydes.
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.
100%) O O H O H O BINAL-H (Noyori) - Chiral aluminium hydride for the asymmetric reduction of prochiral ketones OH OH 1) LiAlH4 2) ROH H O Li + Al O OR R= Me, Et, CF 3CH 2- BINOL BINAL-H O O O BINAL-H,THF Tetrahedron 1990, 46 , 4809 -100 to -78°C HO (94% ee) Intermediate for 3-Component Coupling Strategy to Prostaglandins I O Li+ O CO 2Me RO Li+ RCu RO OTBS O OTBS O CO 2H CO 2Me HO RO OTBS OH PGE 2 REDUCTIONS Alane 50 AlH3 LiAlH 4 + AlCl3 → AlH3 - superior to LAH for the 1,2-reduction of α,β-unsaturated carbonyls to allylic alcohols OMe Ph 1) AlH3, ether, 0°C 2) H3O + O O HO O Me O JACS 1989, 111 , 6649 Me O OH O Diisobutyl Aluminium Hydride DIBAL or DIBAL-H Al H - Reduces ketones and aldehydes to alcohols - reduces lactones to hemi-acetals O Al O OH CHO work up DIBAL O (CH 2)n O OH O (CH 2)n (CH 2)n (CH 2)n lactol (stable complex) - reduces esters to alcohols - under carefully controlled reactions conditions, will partially reduce an ester to an aldehyde Al O DIBAL R CO 2Me if complex is unstable R C OMe fast R CHO R CH 2 OH H if complex is stable R CHO O O O OBn O DIBAL, CH 2Cl 2 O HO OH HO HO H O HO OBn O OBn OH OBn OH JACS 1990, 112 , 9648 OBn OBn DIBAL, CH 2Cl 2 CO 2iPr iPrO2C OHC OBn O R OBn O TMS-Cl, Et3N OH CHO CH2Cl2 R O DiBAl-H OSiMe3 CH2Cl2, -78°C TL 1998, 39, 909 R H Reduction of O-Methyl hydroxamic acids O R O R'-M R' R O OMe N Me TL 1981, 22 , 3815 DIBAL or LAH R H REDUCTIONS 51 Sodium Bis(2-Methoxyethoxy)Aluminium Hydride REDAL Organic Reactions 1988, 36, 249 Organic Reactions 1985, 36, 1.