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The diazoketones 2 have been synthesized by diazo transfer reaction with 2-azido-3-ethylbenzthiazolium tetrafluoroborate.The rhodium-catalyzed decomposition of compounds 2 in tert-butyl alcohol at 130 deg C furnishes the reductone monoethers 3 and after deprotection the aci-reductones 4.Methylation of compounds 4 with diazomethane proceeds stepwise leading first to the monoethers 5 and then to the diethers 6.The thiolactone 4b and even more the lactams 4c and 4d are stronger reducing agents than the lactone 4a. – Key Words: 2,4-Oxolandiones / 2,4-Thiolandiones / 2,4-Pyrrolidindiones / Reductones / Diazo compounds

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Reference：
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem