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Download Acidic and Basic Reagents , Handbook of Reagents for Organic by Hans J. Reich, James H. Rigby PDF

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By Hans J. Reich, James H. Rigby

Recognising the severe want for bringing a convenient reference paintings that bargains not just with the preferred reagents in synthesis to the laboratory of practicing natural chemists, the editors of the acclaimed 'Encyclopedia of Reagents for natural Synthesis' (EROS) have chosen crucial and helpful reagents hired in modern natural synthesis.

This e-book provides articles at the such a lot basic and flexible reagents for effecting natural variations that have been initially integrated in EROS. In determining candidate entries for inclusion during this specific assortment, the editors followed a wide set of standards for outlining what precisely constitutes an acidic or simple reagent.

Each article comprises the entire info present in EROS in addition to improved comparable reagents listings. extra new listings of lately released evaluate articles and monographs are incorporated, in addition to appropriate 'Organic Syntheses' approaches that take care of both the arrangements or reactions of the featured reagents. This thorough and accomplished guide could have frequent attraction.

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Shiner, V. ; Fernandez, V. P. JACS 1963, 85, 2318. 3. Worrall, I. J. J. Chem. Educ. 1969, 46, 510. 4. Woodward, R. ; Wendler, N. ; Brutschy, F. J. JACS 1945, 67, 1425. 5. Hoffsommer, R. ; Wendler, N. L. CI(L) 1964, 482. 6. Hach, V. JOC 1973, 38, 293. 7. Picker, D. ; Andersen, N. ; Leovey, E. M. K. SC 1975, 5, 451. 8. ; Undheim, K. JCS(P1) 1986, 849. 9. Doering, W. ; Young, R. W. JACS 1950, 72, 631. 10. ; Sarker, G. JIC1967, 44, 165. 11. ; Yamamoto, H. JACS 1991, 113, 7074. 12. ; Yamamoto, H. SL 1993, 127; JACS, 1993, 775, 10695.

Removal of the chiral auxiliary, followed by base-catalyzed βelimination of the resulting β-alkoxy ketone, easily gives an opti­ cally pure alcohol in good yield. Several examples of the reaction are summarized in Table 1. Table 1 Reductive Cleavages of Acetals Using Al(OC6F5)3 Catalyst R1 R2 C5H11 Me Me Me Me Et Me i-Bu i-Pr Ph Ph c-Hex Yield (%) 83 61 90 71 78 89 Ratio (S:R) 82:18 73:27 94:6 >99:1 92:8 95:5 Although the detailed mechanism is not yet clear, it is assumed that an energetically stable tight ion-paired intermediate is gener­ ated by stereoselective coordination of Al(OC6F5)3 to one of the oxygens of the acetal; the hydrogen atom of the alkoxide is then transferred as a hydride from the retentive direction to this depart­ ing oxygen, which leads to the (S) configuration at the resulting ether carbon, as described (eq 12).

1971, 18, 1. (b) McKervey, M. A. CSR 1974, 3, 479. (c) McKervey, M. A. T 1980, 36,971. 46. ; Shima, K. JACS 1989, 111, 3707. ; Calas, R. TL 1976, 2449. ; Calas, R. TL 1976, 1871. ; Taddai, M. JOC 1988, 53,911. ; Maruyama, K. JOC 1983, 48, 1564. ; Morgan, I. SC 1988, 18, 1783. ; Narisada, M. JOC 1984, 49, 5271. 47. 8. 11. ; Koyama, K. CC 1985, 287. 12. ; Koyama, K. JCS(P1) 1990, 321. 13. 17. ; Wilhelm, E. JACS 1986, 108, 7767. ; Tan, L. K. JOC 1985, 50, 2796. ; Striepe, W. JOC 1983, 48, 1159. (a) Ansell, M.

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