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Additional info for Advanced Problems in Organic Reaction Mechanisms
C1 a / R 28 Advanced Problems in Organic Reaction Mechanisms 51. A Radical Cascade from a Ketene Dithioacetal Given the selection of an appropriate substrate, the generation of a carbon centred radical from such a substrate can initiate a series of bond-making and bond-breaking processes which are sometimes referred to as radical cascade reactions. These can be of great synthetic value. Thus, treatment of the ketene dithioacetal 1 with a five fold excess of tributyltin hydride in hot benzene under nitrogen and in the presence of a catalytic amount of AIBN gave the metallated benzo[ b]thiophene 2, itself a valuable synthetic intermediate, in 70% yield.
Give a mechanism to account for this oxidation. 70. r with Rhodium(II) Acetate There has been great interest in recent years in methods for the generation of azomethine ylides and in exploitation of these reactive species in tandem/cascade processes for the rapid assembly of polyaza, polycyclic, multifunctional systems, tx-Diazo ketones have featured greatly in such studies, treatment with a catalytic amount of rhodium(II) acetate generating transient rhodium carbenoids. A very common feature of many investigations of this type is the occurrence of quite unexpected reactions.
Biosynthetic studies using 13C and 14C labelled precursors established that 1 is derived from three mevalonates, five acetates and one nicotinic acid, and a degradation method described as "unique" was used to reisolate the intact labelled nicotinic acid precursor from 1 produced in a culture broth of Aspergillus fumigatus. Thus, 1 produced from [carboxy-14C]nicotinic acid was oxidised to the 13-oxo derivative with Jones's reagent, and the ketone was treated with sodium methoxide. After appropriate work-up and purification, [carboxy-14C]-nicotinic acid containing all of the original label was isolated together with the inactive pyrone 2.
Advanced Problems in Organic Reaction Mechanisms by McKillop
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