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Download Designing Organic Syntheses: A Programmed Introduction to by WARREN STUART PDF


Teaches scholars to exploit the language of sythesis without delay (utilizing the grammar of synthon and disconnection) instead of translating it into that of natural chemistry.

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6. 6a). It was postulated that the cleavage reaction presumably occurred via a pathway similar to that in the Cope rearrangement. The iminium ion 3 would undergo [3,3]-sigmatropic rearrangement to another iminium ion (4), which upon hydrolysis produces homoallylamine and benzaldehyde. The aza-Cope rearrangement is synthetically useful because the rearrangement occurs under mild reaction conditions, and [3,3]-sigmatropic rearrangement typically proceeds with a high level of stereocontrol. 4 equiv) (97%) O O H 1.

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5 , Chap. 2; (b) Ireland, R. -N. J. Org. Chem. 1991, 56 , 3572. 3. ; Srebnick, M. Aldrichimica Acta 1993, 26, 17. 4. Ireland, R. ; Wilcox, C. S. J. Am. Chem. Soc. 1980, 102 , 1155. 5. Ireland, R. ; Anderson, R. ; Fitzsimmons, B. ; McGarvey, G. ; Wilcox, C. S. J. Am. Chem. Soc. 1983, 105 , 1988. 6. Still, W. ; Schneider, M. J. J. Am. Chem. Soc. 1977, 99 , 948. 7. (a) Grieco, P. ; Gilman, S. J. Org. Chem. 1980, 45 , 3537; (b) Martinez, G. ; Grieco, P. ; Srinivasan, C. V. J. Am. Chem. Soc. 1982, 104 , 1436.

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