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

By L. Louis Hegedus, Leroy G. Wade

Compendium of natural man made equipment, Vols. I & II by way of Ian T. Harrison & Shuyen Harrison quantity I a whole one-volume compilation of natural practical team differences. comprises 3000 artificial tools offered within the type of reactions with prime references. Divided into sections similar to all attainable interconversions among the foremost sensible teams: acetylene, carboxylic acid, alcohol, aldehyde, and so forth. different elements take care of the security of carboxylic acids, alcohols, aldehydes, aminos, and ketones. 1971 529 pp. quantity II provides the arrangements for all monofunctional compounds released among 1971 and 1974, plus findings of previous years to supply a worthy complement to quantity I. 1974 437 pp.

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5 83% Synthesis (1976) 457 il Ph-C-OCH2CH2Cl Co( 1)phthalocyanine r PhCOOH 66% Angew I n t Ed (1976) 3 681 Use of t h e t r i m e t h y l s i l y l group t o p r o t e c t t h e carboxyl f u n c t i o n o f penic i l l i n s u l f o x i d e s d u r i n g t h e i r conversion t o deacetoxycephalosporins. ( H@ 2 1346 ( s t a b l e t o carbanions) JOC (1974) 2 2787 SECTION 30A PROTECTION OF CARBOXYLIC ACIDS 23 CH200CPh CH2C1 i I 'CH3S @ JACS (1974) 96 590 Use of TlOR t o cleave p r o t e c t e d p e p t i d e s from M e r r i f i e l d r e s i n .

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).

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.

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