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Additional info for Advanced Problems in Organic Reaction Mechanisms
Treatment of A with methoxide gave the highly functionalised octahydroacridine 3 in 90% yield. Identify the pentacycle A and give mechanisms for (a) its formation, and (b) its conversion into 3. NCO o CI MeCO Cl CO2Me OH MeO2C CO2Me 1 2 3 49 Advanced Problems in Organic Reaction Mechanisms Lewis Acid-Catalysed Cyclopropyl Ketone 87. Rearrangement In studies directed towards potential routes to the 11-oxosteroid framework it was found that treatment of the ketene dithioacetal 1 with tin(IV) chloride in benzene at 20~ followed by aqueous quench led directly to 2 in 82% yield.
Lactone Ammonolysis The lactone 1 was subjected to ammonolysis by treatment at room temperature for 5 hours with ethanol saturated with ammonia in the expectation that simple ring opening would occur. The product was not, however, the expected amide; instead, two products were formed, the amide 2 and (R)-lactamide, in almost quantitative yield. An unstable intermediate could be isolated and was shown to serve as precursor to 2. Suggest a mechanism for the formation of 2 from 1. /. O O O Me O NH 2 Me 1 2 R = PhCH 2 74.
The (E) isomers of 1 rearranged much faster than the (Z), and their disappearance followed first order kinetics. Suggest a mechanism for this unexpected rearrangement. OTBDMS OCH 2SMe Rr (E" Zca. 9:1) 1 R1 2 Advanced Problems in Organic Reaction Mechanisms 22 41. Nucleophilic Additions to a Heterocyclic o-Quinone "Heterocyclic o-quinone cofactors" have been a subject of great interest during the last fifteen years, and PQQ, 1, in particular has been the objective of intensive study. It is a growth stimulating substance for microorganisms, is nutritionally important for mammals, and is the redox cofactor of an important class of dehydrogenases.