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Compendium of Organic Synthetic Methods [Vol 4] by L. Wade

By L. Wade

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Can J Chem 56, 1177 (1978) SECTION 39 ALCOHOLS AND PHENOLS FROM ETHERS AND EPBXIDES BupCuLi 43 * T e t r L e t t , 3407 (1977) T e t r L e t t , 1503 (1979) 85% 10% C U I T e t r L e t t , 4069 (1978) 44 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 4 SECTION 40 Section 40 Alcohols and Phenols from Halides >c/ Br 1) Mg, THF 2) Moo5, pyr, HMPA * OH 70% Also works with aromatic halides. ,) LiAlH4 OH BU-CHCH~ JOC 43, 4255 (1978) 3 8% SECTION 40 45 ALCOHOLS AND PHENOLS FROM HALIDES 1 ) NaH, CH2(COSEt)2 * BzCl 2 ) Raney N i 45% BzCH2CH20H Can J Chem 57, 2522 (1979) PhCHO , E t 2 A 1 C1 -Zn CH (OH) P h CuBr, THF 100% JACS 99, 7705 (1977) 1 ) PhCH2MgC1 95% 2 1f i M g B r 3) H20 Et T e t r L e t t , 51 79 (1978) 46 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 4 1) 2) Bu2CuLi Me1 * SECTION 41 WMe 96% JACS 99, 5816 (1977) S e c t i o n 41 A l c o h o l s and Phenols f r o m Hydrides - Angew I n t Ed 18, 407 (1979) Angew I n t Ed 18, 68 and 69 (1979) Review: "Superacid-Catalyzed Oxygenation of A1 kanes" Angew I n t Ed 17,909 (1978) SECTION 41 ALCOHOLS AND PHENOLS FROM HYDRIDES 47 64% electrocatalysis Chem Ber s,3561 (1977) Synthesis, 215 (1978) Benzeneseleneni c OAc OAc Chern Lett, 763 (1979) 48 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 4 - SECTION 42 1 ) LDA 2) 7n% Moo5, Pyr, HMPA k 4 M e same conditions d i j - O M e 74% JOC 43, 188 (1978) Section 42 Alcohols from Ketones COOMe CeCl CHO NaBH4 * OH CHO - JACS 101, 5848 (1979) 75% S E C T I O N 42 ALCOHOLS FROM KETONES -a 49 PH 0 Na2S204 H20/di oxane 80% Synthesis, 246 (1977) dl 0 2 -pro pa no 1 + alumina HO 90% JOC 42, 1202 (1977) NaH, L-AmONa 90% Ni ( O A C ) ~ J O C 43, 4804 (1978) T e t r L e t t , 1069 ( 1 977) OH 0 BH~OH~ -6 JOC 42, 3963 (1977) 86% 50 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 4 n-C6H1 0 II 3-C-Me NaBH4, SECTION 42 PH A1203 g-C6H, 3-CH-Me ether 90% S y n t h e s i s , 891 (1978) 8 j?

Removed by p h o t o l y s i s i n e t h a n o l o r by Zn/HOAc. 5) t o remove e t h y l e s t e r b l o c k i n g groups i n p e p t i d e s y n t h e s i s . JACS 101, 3394 (1979) SECTION 30A PROTECTION OF CARBOXYLIC A C I D S 27 Use o f Maq e s t e r s i n pept ide synt h e s i s : 0 Prepared using Maq-OH and DCC; removed by sodium d i t h i o n i t e , p h o t o l y s i s , o r polymer-bound 9,l O-di hydroxyanthracene. Soluble i n organic solve n ts , and UV-active a l l o w i n g f a c i e d e t e c t i o n on TLC.

JACS 101, 3394 (1979) SECTION 30A PROTECTION OF CARBOXYLIC A C I D S 27 Use o f Maq e s t e r s i n pept ide synt h e s i s : 0 Prepared using Maq-OH and DCC; removed by sodium d i t h i o n i t e , p h o t o l y s i s , o r polymer-bound 9,l O-di hydroxyanthracene. Soluble i n organic solve n ts , and UV-active a l l o w i n g f a c i e d e t e c t i o n on TLC. T e t r L e t t , 103 Review: (1 977) " A c t i v a t i o n and P r o t e c t i o n o f t h e Carboxyl Group" Chem & I n d , 610 (1979) Rev ew: " P r o t e c t i n g Groups n Peptide Synthesis" Chem & Ind, 617 (1979) Other r e a c t i o n s useful f o r t h e p r o t e c t i o n o f c a r b o x y l i c a c i d s a r e i n cluded i n Section 107 (Esters from Carboxylic Acids and Acid H a lides) and Section 23 (C a rb o x y l i c Acids from E s t e r s ) .

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