By Michael B. Smith

Content material: Preface. Abbreviations. Index, Monofunctional Compounds. Index, Difunctional Compounds. advent. 1 guidance of Alkynes. 2 coaching of Acid Derivatives. three instruction of Alcohols. four arrangements of Aldehydes. five instruction of Alkyls, Methylens, and Aryls. 6 training of Amides. 7 training of Amines. eight instruction of Esters. nine instruction of Ethyl Epoxides and Thioethers. 10 instruction of Halides and Sulfonates. eleven instruction of Hydrides. 12 practise of Ketones. thirteen education of Nitriles. 14 education of Alkenes. 15 guidance of Oxides. sixteen coaching of Difunctional Compounds. writer Index

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NaBH4 (solid state) PhJ Ph PhJ 3d Ph 63% Toda. ; Yagi, M. Angew. Chem. Int. , 7989,28, 320. 5 H20 R~C12(PPh3)3, RT Ph 24h Khai. FLT,; Arcelli, A. J. Org. , 7989, 54, 949. BnEt3NCl, NaBH4 aq. THF, 1% Montmorillonite clay aq. NaHCq &&ar. M. Synth. , 7989,79, 2313. 9 6 Oo/ 44 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 7 Ph ph ZnCl2, Zno , EtOH , 1h * ref lux 4 f0 Toda. ; Tange, H. J. Chem. ,Perkin Trans. I, 1989, 1555. ; Bakthavatchalam, R . ; m . R ~ BOrg. Prep. Proceed. , 1989, 21, 373. ; Perichon, J.

An. B. , 1988, 29, 4847. OMOM -78OC , 5rnin 2. sald NH&I 93% Johnson. R. J. Org. ; Karniya, Y . J. Am. Chem. , 1989, 1 1 7 , 4392. SECTION 42B Alkylation of Ketones 47 (25:l) U o ;Kenny, C. J. Am. Chem. ,1989, 11 1,8236. &Lmder. ; Kenny, C. , 1987, 28, 4367. BuzCuLi , THF Me3s575% ___7 2 eq. Me3SiCI Matsuzawa, S . , 7989, 30, 1975. 3% aq. ; Inanaae. ; Yamaguchi, M. , 7989, 30, 2837. , 1989, 30, 5533 (Yo ;($A THF , ,6OoC 10% ZnCI2 =rc' 8 1% Cahiez. -Y. , 1989, 30, 7373.

SECTION 30A: PROTECTION OF CARBOXYLIC ACID DERIVATIVES 1. Teo , NaBH4 , EtOH Ph'f@*~~ 0 2. aq. ; Zhou. -J. Synfh. , 7987, 17, 161. * Ph-COOH 8 5 Yo COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 7 14 c NHBOC '' , ~ CI o ~ o NHBOC ~ CI NEb , CH2C12, RT ,2h '%OH SECTION 3 OA 0 2. ; Martinez. -P. J. Org. , 1987, 52, 2364. 1. HOCH2CH2CN, cat. DMAP CH2ChI DMF O 'H B O C N H ~ Me 2. DCC , CH2C12 + 9 3% JoPCN > BOCNH 1. MeOH , 10% aq. K2CO3 Me R T , 10 min 8 0 % 2. ; Katti. S R . , 1989, 30, 3569. PhCQM ' 1 .

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