By Chiara Ghiron, Russell Thomas
This e-book is made from a chain of workouts in artificial natural chemistry established round lately released syntheses. each one workout supplies a connection with the unique paintings, an artificial scheme within which both constructions or reagents were passed over, a chain of questions about the workout, and often references to comparable literature and priceless reviews.
The routines are designed to supply demanding situations for individuals with a variety of backgrounds, from undergraduates to educational employees and business crew leaders, they usually let the readers to extend their vocabulary of man-made changes. Taking a unique procedure, this quantity encourages lively participation; rather than soaking up usual concepts, readers are requested to suggest ideas to set difficulties. The routines are perfect for crew discussions of natural chemistry.
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Additional info for Exercises in Synthetic Organic Chemistry
Further Reading • For a recent study of squarate ester reactivity see: L. A. Paquette and T. Morwick, 7. Am. Chem. , 1995,117, 1451. • For a review, in German, of the reactions of squaric acid and its derivatives see: A. H. Schmidt, Synthesis, 1980, 961. • For a recent application of this rearrangement to 4-allenylcyclobutanones see: M. Taing and H. W. Moore, J. Org. , 1996, 61, 329. 47 34. The Synthesis of (±)-12a-Deoxytetracycline G. Stork, J. J. La Clair, P. Spargo, R. P. Nargund and N. Totah, J.
Condon, J. Org. , 1993, 55, 1030. 9 Abstracted with permission from J. Org. , 1993,58, 1030 ©1993 American Chemical Society Discussion Points • What is the mechanism of step d? • Give reasons for the use of two equivalents of Lewis acid in step e. • During the ene reaction of step f, a regioisomer of 6 could, in theory, be formed. Propose a structure for this isomer and suggest a reason why its formation was not observed. • Explain the stereoselectivity in steps h and j. • Suggest a possible reason why the phenylselenation reaction of step o required acid catalysis.
When NaH was used as the base in the palladium-catalysed alkylation step a, no enantioselectivity was observed. An enantioselective reaction was obtained with the use of a lithium base or alternatively via the transformation of 2 into its silylated derivative 6. Propose an explanation for this finding. • What is the mechanism of step d? Further Reading • For a review on the selectivity in palladium-catalysed allylic substitutions, see: C. G. Frost, J. Howarth and J. M. J. Williams, Tetrahedron: Asymmetry, 1992, 3, 1089.
Exercises in Synthetic Organic Chemistry by Chiara Ghiron, Russell Thomas