By Michael B. Smith
Compendium of natural man made equipment quantity III Louis S. Hegedus & Leroy G. Wade, Jr. offers the recent man made tools for practise of monofunctional compounds for 1974, 1975, and 1976. Sections correspond to many of the attainable interconversions among the main useful teams. furthermore, the quantity includes examples of recent tools of guidance of difunctional compounds shaped from pairs of the foremost sensible teams. 1977 (0 471-36752-4) 495 pages Compendium of natural artificial tools quantity II Ian T. Harrison & Shuyen Harrison ". a priceless complement to their previous quantity. not just does it comprise many extra examples of equipment of getting ready monofunctional compounds, however it additionally features a new part masking practise of difunctional compounds.. relatively priceless for the bogus natural chemist who needs to find particularly speedy a recipe for an easy sensible team transformation." --Laboratory perform 1974 (0 471-35551-8) 437 pages Compendium of natural artificial equipment quantity I Ian T. Harrison & Shuyen Harrison A compilation of natural practical team differences, together with 3000 man made tools awarded within the kind of reactions with prime references. Divided into sections akin to all attainable interconversions among the main sensible teams: acetylene, carboxylic acid, alcohol, and so on. different components take care of the safety of carboxylic acids, alcohols, aldehydes, amines, and ketones. "A very usable quantity . merits a large sale." --Journal of the yank Chemical Society 1971 (0 471-35550-X) 529 pages
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Extra resources for Volume 4, Compendium of Organic Synthetic Methods
Example text
Rboxylic No additional examples Acids from Nitriles CARBOXYLIC A C I D S FROM OLEFINS SECTION 29 S e c t i o n 29 21 C a r b o x y l i c Acids from O l e f i n s C8H1 7-CH=CH2 KMn04 ,HOAc 94% w C8H17-COOH H2° JOC 42, 3749 (1977) 1 ) 03 n -C6H1 3CH=CH2 2 ) H2/Pd, CaC03, PbO JOC (USSR) n-C H COOH 6 13 14,48 (1978) 98% 2 ) H2, L i n d l a r B u l l Akad USSR Chem 2)NaI04 ,NaHC03 HO 3 , C6H13NH29 A 4 ) KOH, H20 81% 25, * H e l v Chim Acta 1790 (1977) 77% 61,2286 (1978) 22 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL S e c t i o n 30 4 SECTION 30A Carboxyl ic Acids from M i s c e l l aneous Compounds Li I 1) PhOCHCOOLi 2 ) NaOH, H202 * Bu3B Bu-CH2COOH 100% T e t r L e t t , 2891 (1978) 1 ) BuMgBr, N i C l 2THF 2 ) H+J 0 Ph U O 92% 99%ee he BCS Japan 51, 3368 (1978) c Section 30A P r o t e c t i o n o f Carboxylic Acids 1 ) KOH 2 ) C1 CH2SMe, NaI , 18-crown-6 * R-COOH H w 0 It R-C-OCH2SMe 1 ) NH4Mo03, H202 o r CH31 T e t r L e t t , 731 (1978) T e t r L e t t , 689 (1979) PROTECTION OF CARBOXYLIC ACIDS SECTION 30A 23 9, 267 (1979) Synth Corn - 1) BrZnCH2COOEt + Y O Br O H /yPI 2 ) H2C(OMd2 88% ocH20cH3 Br S y n t h e s i s , 567 (1977) CHzCH2SCH3 CH2CH2SCH3 H2N-CH-COOH I TsOH, C1 3C-CH20H * 8 I H3N-CH-l-OCH2CCi CC14, a z e o t r o p i c d i s t .
JOC 44, 3969 (1979) 88%ee JACS R-CDO 1 )3-pinanyl-9-BBN * 2)HOCH2CH2NH2 R = a1 k y l , a r y l 99, 5211 (1977) 0" RWC-D I H %80% 58-86%ee ,ally1 JACS 101, 2352 (1979) Bu-CHo BuMnI acetone * Bu2CHOH T e t r L e t t , 3383 (1977) 89% 34 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 4 O " \ '0 A1 / SECTION 34 H 'OEt H Ph-CDO 75% JACS CH3CH2CH0 1 )CH2=CHCH2B(C4H9)2 2) triethanolamine x,3129 (1979) + CH3CH2 \iii OH Bull Acad USSR Chem R = a1 kyl 82%ee , Ph 27, 1663 (1 979) Me Angew Int Ed 3,306 (1979) SECTION 34 35 ALCOHOLS FROM ALDEHYDES B u 3 S n N Ar-CHO * Ar %go% BF3*Et20, CH2C12 A r = Subst.
JOC R-C-OBZ 7 , 251 98% A1 C1 b 43, 4194 (1978) R-COOH PhOCH3 T e t r L e t t , 2793 (1979) peptide - 25 PROTECTION OF CARBOXYLIC A C I D S SECTION 30A * Bzl peptide-OH Pd/ C JCS p e r k i n I,490 (1977) Na2S R-COOH TH F R = Azetidinone JOC 43, 1243 (1978) 0 II R-C-OCH2CH2X NaHSe RCO8 o r 1 ) Me3SnLi 2 ) Bu4NF X = C1 , B r fi pep t ide -C-0- CH2 - CH2Br Synth Comm 1) NaI , DMF * g, 301 and 359 (1978) peptide-COOH 2) Zn Chem Ber 112,2145 (1979) 26 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 4 SECTION 30A Use o f t h e e-methoxyphenacyl a c i d p r o t e c t i n g group i n g i b b e r e l l i n synthesis.