Download Compendium of Organic Synthetic Methods Volume 3 by L. Louis Hegedus, Leroy G. Wade PDF

By L. Louis Hegedus, Leroy G. Wade

Compendium of natural man made tools, Vols. I & II by way of Ian T. Harrison & Shuyen Harrison quantity I a whole one-volume compilation of natural sensible staff adjustments. contains 3000 man made equipment offered within the type of reactions with best references. Divided into sections equivalent to all attainable interconversions among the main useful teams: acetylene, carboxylic acid, alcohol, aldehyde, and so forth. different components care for the safety of carboxylic acids, alcohols, aldehydes, aminos, and ketones. 1971 529 pp. quantity II offers the arrangements for all monofunctional compounds released among 1971 and 1974, plus findings of past years to supply a beneficial complement to quantity I. 1974 437 pp.

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Occur i n t h e ROH ( R = a l k y l o r a r y l ) see l i t e r a t u r e . For r e a c t i o n s o f t h e type RH Section 41 (Alcohols and Phenols from Hydrides). -f S e c t i o n 36 Alcohols and Phenols from Amides No a d d i t i o n a l examples S e c t i o n 37 Alcohols and Phenols from Amines No a d d i t i o n a l examples S e c t i o n 38 P h- C- OMe Alcohols from Esters NaBH4, HSCH2CH2SH r PhCH20H THF, r f x 20 h r s . T e t r L e t t (1975) 3295 100% ALCOHOLS AND PHENOLS FROM ETHERS AND EPOXIOES SECTION 39 Na@[OBH 3C ( CH3) NPh PhCH2CH2COOEt p Ph(CH2)30H CH2C1 97% Chem Pharm B u l l (1976) &NHCHRCOOE t 33 41059 NHCHC-R' 1 ) 3 eq R'MgX R OH 2 ) H20 "excellent yield" Comptes Rendus R e l a t e d methods: S e c t i o n 39 C (1975) 280 123 C a r b o x y l i c A c i d s f r o m E s t e r s - S e c t i o n 23, P r o t e c t i o n o f Alcohols - S e c t i o n 45A A l c o h o l s and Phenols f r o m E t h e r s and Epoxides H I , NaI OMe + 84% CH30CHC12 OH JOC (1976) 41 367 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 3 34 SECTION 39 JCS P e r k i n I (1976) 2237 A d d i t i o n a l examples o f e t h e r cleavages may be found i n S e c t i o n 45A ( P r o t e c t i o n o f Alcohols and Phenols).

CH3C( Bu) 20H F A JOC (1975) 3) NaOH, H202 1) Bu2BH MeCECEt BU 2 ) MeLi f 3 ) HC1 4) 40 2845 NaOH/H2OZ 1 MeCH2C -E t 70% I OH S y n t h e s i s (1974) 339 24 SECTION 32 ALCOHOLS FROM CARBOXYLIC A C I D S S e c t i o n 32 25 A l c o h o l s from C a r b o x y l i c A c i d s 00 Bu4N BH4 PhCOCi > PhCH20H 100% JOC (1976) CH2CHCOOH Me0 * BIr NH2. MeSH + B(OMe)3 - PhCH20H JOC (1974) RCOOH + Ph 1) Et3N 3 3052 RCH20H t 2 ) NaBH4 JOC (1974) 39 111 80-100% COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 3 26 1 ) BuLi, -100' CH2C1 &- 2 ) PhCOC1, -78" 3 ) MeOH/HOAc PhC-(CHC12)2 I OH Chern B e r (1975) Also via: 108 328 E s t e r s ( S e c t i o n 38) S e c t i o n 33 A l c o h o l s from A l c o h o l s and Phenols Org Synth (1976) S e c t i o n 34 55 1 A l c o h o l s and Phenols from Aldehydes 2 Ph-OMgBr + PhCHO benzene JCS Chem Comm (1976) 309 SECTION 34 SECTION 34 RCHO + 27 ALCOHOLS AN0 PHENOLS FROM ALDEHYDES E t20/HMPA MepCuLi >go% RCHOHMe + (Me0 13P T e t r L e t t (1975) 2353 Me3Si CH2CH=CH2 CH3( CH2) 2CH0 T i C1 CH2C1 dH T e t r L e t t (1976) 1295 PhCHSH 1 ) BuLi PhCH2SH - 1 I 70% CH(OH) 2) PhCHO Ph Angew I n t Ed (1974) Me2NCH2CO2-L-Bu 1 ) LDA, -78" 2) CH3CH0 r 2 202 CH3CH (OH) CHCO2-L-Bu 8 5% I NMe2 T e t r L e t t (1975) 1477 PhCHO +'& '0 - 1 ) TiC14, CH2C12 2) MeOH PhCH( OH)CH2COCH2 t COOMe Chem L e t t (1975) 161 91% SECTION 34 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 3 28 MeCOCCl I ) LDA, THF, -75" 2 ) EtCHO MeCOCCl f 73% I CH( OH) E t Bull SOC Chim France (1975) 1876 MeN (NO )Me 1 ) LDA, THF, -80" + MeN( NO)CH2CH(0H)Ph 85% 2) PhCHO Chem Ber (1975) I ) LDA / NMePh MeCH=C C' N 2) PhCHO t 1293 ,NMePh PhCHCH2CH=C I 81 % C' N OH Syflthesis (1975) 512 PhCHO + n-Bu3SnCC13 1) 80" 2 ) H20 PhCHOHCC13 63% J Organometal Chem (1975) Cl3CC0 - i - P r 2 - 1 ) Et2NLi, THF-OH-HMPA 2 ) Me2CHCH0 t 102 Me2CHCHCC l2COz-I-Pr I OH Synthesis (1975) 524, 533 423 77% SECTION 34 1 ) LDA, THF/Et20, -90" CH2Br2 29 ALCOHOLS AND PHENOLS FROM ALDEHYDES PhCH-CHBr2 + 63% I 2) PrCHO OH B u l l SOC Chim France (1975) 1797 PhCHO + CHC13 t-BUOK, NH3.

NaOH Me I 97% P hCHCH20H S y n t h Comm (1976) S e c t i o n 41 SECTION 41 a 349 A l c o h o l s and P h e n o l s f r o m H y d r i d e s Fe", Cut+ Ph-OH JACS (1975)97 1603 JCS Chem Comm (1975) 36 64% SECTION 41 39 ALCOHOLS AND PHENOLS FROM HYDRIDES 51% y i e l d 11% conversion J O C (1976) 41 2651 72% J O C (1975) Q 2141 Y 1 ) LDA, THF 2) Yo" + +30% o2 OOH 3) H30+ J O C (1976) fl 370 OH I Rec Trav C h i m (1976) 95 285 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 3 40 Review: SECTION 42 Photochemical H y d r o x y l a t i o n o f Aromatic Compounds S y n t h e s i s (1974) 173 S e c t i o n 42 A l c o h o l s f r o m Ketones JOC (1976) 1 3 2 0 9 Me2C0 + BrCH2CMe=CHCOOEt 1 ) Z n , HgJ2 t Me#( OH)CHCMe=CH2 I COOEt 2) 3 ) H@ J Organometal Chern (1975) 70% 96 149 H MeLi -Me2CuLi 91% E t 2 0 , -70" ( h i g h y i e l d a x i a l OH) JACS (1975) 97 5280 SECTION 42 41 ALCOHOLS FROM KETONES JCS Chem Comm (1975) 892 f e t r L e t t (1975) 3897 Review: S t e r e o c h e m i s t r y o f O r g a n o m e t a l l i c Compound A d d i t i o n t o Ketones Chem Rev (1975) 75 521 T e t r L e t t (1975) 1811 42 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 3 LiAl (E-B~)~OR YH3 P h -C -E- Bu + PhCOCH3 SECTION 42 I OH R = (-)-N-methylephedrine 56% 31% ee T e t r L e t t (1976) 4781 1 ) BuLi, THF-hex.

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